Tara Wilson Helps Us Find and Prioritize Humanity in Digital Transformation

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In this episode of Relationships at Work, Russel chats with digital transformation consultant and executive coach Tara Wilson on prioritizing the human element of digital transformation and change management.

A few reasons why she is awesome  —  she is a speaker and executive coach, the director of Client Partnership at Rangle.io, partnering with enterprises to build digital experiences, while also leading her own consultancy, helping organizations with transformational change and program management. She’s spent the last 20+ years helping organizations with their digital transformation on various projects and initiatives, including Blackberry, MobiStream, and MCAP Commercial Limited.

Connect with, and learn more about Tara on…



  • Who needs to be considered in digital transformation.
  • How you bring employees along into this change management.
  • The role vision and mission have in communicating change.
  • Where to start when introducing digital transformation into your organization.
  • How curse of knowledge can get in the way.
  • How you know you’re successful in transformation.

“Change cannot be imposed. It must be worked through, if you really want it to work.”

Tara Wilson


Russel Lolacher: And on the show today, we have Tara Wilson and here is why she is. Awesome. She is a speaker, executive coach. She’s the Director of Client Partnership at Wrangle.Io that partners with enterprises to build digital experiences while also leading her own consultancy, helping organizations with transformational change and program management.

She spent the last 20 plus years helping organizations with their digital transformation on various projects and initiatives, including BlackBerry, MobiStream and MCAP Commercial Limited. Hello Tara.

Oh, it’s all fun and giggles now, but wait, we get into our topic of digital transformation today.

Tara Wilson: Okay,

Russel Lolacher: I’m super excited, but before we get there, we have to ask the question I ask all of my guests, which is what’s your best or worst employee experience?

Tara Wilson: Okay I don’t know if I’m gonna get double points for this, but I’ll talk about one experience that was my best and worst experience. It was a little bit of a mind blowing experience. So I was working at one of the companies that you mentioned doing cloud transformation and we were putting in the first cloud and it was stalled for a number of months and we couldn’t figure out why.

So I came in, got on board and I canceled a whole bunch of stuff. I said, that’s detracting from what we’re trying to do. We’re not doing it. We got, we got things rolling and within four months we had a working cloud. And then I was tasked by my VP to get all of the other VPs of the impacted areas in a room together and congratulate them a big celebration.

We got a cloud up and running. And so, I said, do you want to have a few words? And I said, yeah, absolutely. So I looked around and I was a little bold and maybe brash when I was a little bit younger and maybe took some liberties that I shouldn’t have. And I said, okay, well this is great. We’ve got one of our cloud instances up.

That’s wonderful. But. We’re a tech company, so you can guess which company it was. If we couldn’t get this up and running, we’d have some serious issues. But you all need to understand, now the hard work happens. We got it working, now we’ve got to retool, we’ve got to change our end to end processes, we’ve got to retrain, we’ve got to have people happy about retraining, because their bonuses are going to be affected, because they’re just learning something new now.

This is where we need all of you now to start talking to each other and figuring things out. You could have heard a pin drop. Everybody was just looking around going, Oh my God. And my VP was like, thanks. Uh, okay, let’s get to the lunch section, and I was just, it was, it was amazing because we had accomplished something that they were struggling to do, but then it was also the worst moment because I thought, What the hell have I gotten into if these guys are all scared about doing this work?

Who the hell am I to start pulling this stuff together and start leading it? So that’s what really got me on this course of the change management transformation piece of the programs and products that I was delivering because I realized everybody was so focused on the tech. Yeah, we’ve done this.

We’ve accomplished something that everybody thought that that was the end goal. But the end goal is really adoption is really changing how people work and. No one was talking about that.

Russel Lolacher: Ouch. Uh, but it’s so funny because people, especially, well, I mean, people that are busy obviously see things as check boxes, not a journey, right? But we did a thing. We’re excited. We did. We should be celebrating this as opposed to your truth bomb, which is like, Oh, no, no, no, no, no, no. This is a multi year problem.

Not a, not a box that you just checked off and a poster we can put up.

Tara Wilson: Everybody thinks, okay, I’m agile now, I’ve solved it. Great. Okay,

Russel Lolacher: No, no. And it never is. Uh, and that’s the big question we have today with digital transformation, which is what we’re talking about today. And before we get into it, I like defining terms because we don’t do a great job in a lot of organizations with actually defining what the hell we’re talking about.

So let’s first explain what is digital transformation?

Tara Wilson: It varies, as you pointed out across the board. The way that I think about it is thinking about a technology first kind of approach to enabling people to do something. Whether that’s getting them the right data to make data driven decisions, whether that’s getting your customer enough information online so that they can evaluate.

A product or service and make a decision, whether that’s enabling your customer service folks, or people that are talking to the customers to have the right information so that they can actually walk someone through a buying experience or a selection process. I think about those kinds of things, and I, and I think about.

The old world of kind of legacy systems where that’s not my department. You need to talk to this person as opposed to today’s world where it’s, anybody can answer anything because they have the access to the information that they need to make those intelligent decisions and guide customers through things.

Russel Lolacher: Why? So, just the bigger question, which is a lot of organizations. I mean, my God, digital transformation is such a buzzy word now. Like you can throw it in there with innovation and agile and so forth, where it’s this, it’s like you said, you get almost a point by anytime you say it at work, you’re like, it’s is there a scorecard being somewhere I don’t see?

Tara Wilson: The drinking bingo.

Russel Lolacher: Well, literally, like it’s used so much. If you don’t use it five times in an email, you failed at something. So why is it… well, why is that? Why is the profile of it been blown up so much recently?

Tara Wilson: I would say because from a business perspective, the, the golden rule is compete or die. And what we’ve seen now with just the internet being so accessible to everybody, people want information. I almost hate it when I go to any website and it’s these are our service hours, call in between, whatever.

And I’m like… Who wants to do that? I don’t want to waste my time. I want it at my, at my fingertips. So really what’s happened is it’s the consumers that have driven this change across the internet, across anybody selling services or businesses that has really proliferated the business to business experience.

So now it’s not only as a consumer, do I want the information that I need when I, when I want it, I want to be able to shop at three in the morning when I can’t sleep all that kind of stuff, right? That’s what’s going on. And what’s happened now is that expectation has been set as a consumer.

And now when you go into your business world, you think about, Oh, this is what consumers are expecting. And whether that’s a business consumer or an actual just individual consumer, that bar has been raised. So people are now having that expectation. And oftentimes, even if you’re doing any kind of business relationship building, everybody goes to LinkedIn to check them out.

Everybody goes to the corporate website. What are their values? How long have they been here? Who, who do I know from a corporate perspective? Who have they listed here? You’re trying to figure out that pecking order to understand. Am I talking to the decision makers? What’s important to these folks? Are we aligned on business values? Will this relationship or partnership or interaction make sense? So that’s what I’d say about the why.

Russel Lolacher: Fair. And I completely understand that. The problem I have with digital transformation is, and it’s, it’s a problem maybe in a way that organizations generally think customer, they look dollars. Here’s digital transformation. I get that. But this also goes back to the why of my show, which is employees, organizations only seem to give a crap if it’s about the customer, not the employee. And they’re suddenly figuring out that the employee is the gateway to those customers over the last couple of years. So when it comes to digital transformation, sure, I get the why on the other end, but the employees have to be part of that journey or they’ll go somewhere else.

So why is this so hard? Or maybe it’s easy. It’s digital. I don’t think we’d be having a conversation if digital transformation took about three steps and you’re done in 15 minutes.

Tara Wilson: Yeah.

Russel Lolacher: Is this so hard?

Tara Wilson: I think people forget about the human element. I think, to your point, they think about the customer and they don’t think about the employee. One of the things that I thought was interesting is every time that I’m doing something technologically oriented which is 98 percent of the time I also ask How are you talking to your internal teams about this?

I don’t care if they’re impacted by this or not. Is this a strategic goal that the rest of the organization is aware of? Because they need to understand that a group of people is focused on making a change and how they can support that and how there may be a ripple effect to other organizations.

Because now that we have something new involved, other people may want to join that team. Those people may look to expand their knowledge into other areas. So how are we managing that? Because everybody knows it’s so much easier to train up a current employee than to hire somebody new, right? That costs a lot of money.

There’s that. And then there’s also the fact that people forget, every single employee is an ambassador of your company, period, whether that be talking to a client, talking to a family member out there and whatever, going to a job fair to recruit… you’re missing an opportunity if you haven’t turned all of the employees into someone who loves that organization.

And so helping them retrain, I was going through a transformation in another organization just recently, and some people were like, well, I don’t want to learn cloud. I don’t want to learn about platform services. And I said, okay, cool. Well, if you want to just stay in the technology niche that you’re in you need to know it’s going away here.

So this company is actually supporting your retraining internally. Take a look take a look at job postings for that skillset that you’ve got. How many are there? Like when, when technology changes, you need to get on board or you need, or you will be left behind. So think about how do I build resiliency in my workforce?

How do I demonstrate and how comfortable do I feel about changing things? I mean, we’ve talked a little bit before about the fact that technology exists to change. It’s got life cycles. It’s got lifespans. Sometimes it leapfrogs things. Sometimes it just evolves, but we’re here to make changes.

And oftentimes it’s the technology folks who, who are the most apathetic to change and just want to run screaming from it, but I’m like, this is why you have a job, This is what we do.

Russel Lolacher: So what are the ingredients? Before we get into all the challenges and what we need to do better at what is an organization need to have in place for it to be able to adopt digital transformation more easily.

Tara Wilson: I think one thing that it really needs to do is be honest about any silos that are built. So one thing that I’ve seen many times, which is a recipe, maybe not the recipe for success is that it’s led by technology. Oh, we’re doing agile now, everybody. We’re not doing waterfall anymore. We’re going to build these requirements as we go.

We’re going to demonstrate what we’re delivering and we’re going to get constant feedback as we go. We’re agile, but it actually needs to start higher up in the organization to understand that not only does that need to happen, but how you manage budgets needs to needs to change how you take a look at your capitalized versus operational costs.

How you’re looking at staffing for things. All of that needs to be thought through. And needs to be understood at a leadership level, so that people are prepared to take that on when they’re, when they’re transitioning so many times it’s just, well, this is what’s in the business case. The business case says, I have half a million dollars in 6 months. What happens after that? Does this magically just steer its own ship? Is it upgrades are just going to happen, ad hoc? It’s got no life cycle and the lifespan and people need to think about If we’re going to be making this kind of a significant change or investment as an organization, what skills do I need a leadership team to have?

How do we need to be working together? We need to, we need to talk openly about the roadblocks of moving from how we were working to how we’re going to work and literally build a plan for that. Cause it’s not going to happen overnight. You may have people who have been fighting for funding. You may have been people who have different visions of the strategy of how to execute on things.

You need to have very real conversations around this is how we’re moving forward. Get on board or let’s figure out how to maybe exit you gracefully. Because if this is truly what you believe, go and do that somewhere else where that’s what they want to do. Because it, it bleeds through in all the conversations it leads through in departments.

You need to make sure that you have that alignment so that you can have open and honest conversations at every level as you’re going through things because it’s not going to be easy. Change is hard. This is why this is a three step plan, right? So this is where you need to make sure that you have people that you trust, people that are aligned, and people that will support this even through those hard times.

Russel Lolacher: One, I will add to that. I think some organizations miss a step on is defining the why you’re doing it to begin with, because it’s very much, uh, here’s what we’re doing. Here’s the old world. Here’s the new world. Get on board. But there’s that chunk of, if I want buy in, I need to understand why the change is happening, what the new, why the new world will be better.

I think there’s that communications piece. And sometimes I’ve seen, well, it depends on who’s instrumenting that change. And I think that’s the next question I have, which is the change agent. Who is that? Because those digital transformation people, are they technology people, are they service leaders?

Are they people leaders? Are they communications experts? Are they a Jack of all trades? And who the hell is that? Who, what is that person that drives this change? Cause usually it’s not the executive at the top who has all those skills. They’re just the champion of it.

Tara Wilson: Yeah, so that’s a very good point because honestly, if you wanna look at successful changes, everybody needs their manager to be bought in. And a successful change is not done to you. It is done with you, right? So you have typically, you have town halls where you discuss this. What is it gonna mean for my job?

You wanna be able to have those candid conversations with my boss to say, I don’t think I’m comfortable retraining on this stuff starting from ground zero. In a lot of organizations, you have merit based bonus, bonus structures. I used this, this example before when I said, okay, so we’re getting rid of data centers now, cause we’re all going to cloud.

What if this guy is the most expert cabler and racker that you’ve ever seen? It’s a whole new world now going virtual, you’ve got to make that safe for them. You’ve got to make that comfortable. You’ve got to make them understand that this is an option. We’ve got a window to do this. So again, if you’re not comfortable, this is what it looks like.

Why wouldn’t you be? If this is where things are going, let’s talk about that because this is where the demand is. This is where the industry is going. Let’s talk about how this is going to help you build your skills, how this is going to help you learn something new, how this is going to help you become an expert in that new field.

Let’s talk through what that’s going to look like. And let’s put a time window on it. I don’t expect you to be an expert by next review cycle. I expect that we’re going to invest in training. We’re going to then explore doing cause you have to now build those skill sets. So you’re going to be doing that on the job.

You’re going to fail a few times. You’re going to make a few mistakes. Absolutely. That’s okay. We know that, right? You’ve got to build that safe space for that change because you’re right. The CEO at the top or the leaders at the top understand the strategic value of it, but they don’t communicate it a lot.

So oftentimes when I go into organizations, I say, pause. Who knows what about why we’re doing this? Who have you told? Have you allowed them to ask questions about it? Have we had real conversations about it? Because when you’re talking to people en masse, okay, here’s the messaging, here’s the points, here’s the strategic stuff, but you need to go back then and talk to your leaders.

At every level to, to be able to have those candid conversations because that’s how you build change. That’s how you build support and where it’s not one person just leading it. You do need to make sure that you have a change agent in every area so that they can come together and talk about shit. This is what I’m hearing.

Oh, my God, I’m hearing this. Oh, these people are really supporting it. Really? Well, what did you do? How did you do that? So you can share that information and make sure that the messaging is consistent, but still authentic. So it’s okay to address people that are worried about this stuff. It’s okay to say how are we going to get through this together and make sure that oftentimes those are the good questions that can help turn people around from being afraid of things and then saying, oh, they’ve actually thought this through. This isn’t just something being pushed on me there. They care about me as an individual and what I’m going to do. And then you’re able to use that to say, okay, let’s have those, let’s have those open conversations. Is everybody feeling this way? Okay. Let’s talk about that. So you need to focus on the messaging for sure. And that is the 1 step that, that you can’t do enough. I go back to my intro psychology days and it’s people need to hear things on average five times plus or minus two.

So I try to remember that when I’m parenting saying, okay, only six more times to go only five more times to go, right? They’re not going to get it on the first try. You need to know that.

Russel Lolacher: Tell them, tell them again and tell them again.

Tara Wilson: That’s right.

Russel Lolacher: So can expectations and perceptions get in the way from those that are trying to make the change? Because there is this thing where it’s we’re going to change by this quarter, by next fiscal. I’m like, I don’t know about you, but the last time I saw any change management, it was an eight year process, not a fiscal quarterly process.

So how does that get in the way and how do you overcome that? From a change agent standpoint, Tara.

Tara Wilson: So, one of the first things that I do is try to build alignment from the senior leadership level, because you need whatever impacted areas there are, you need anybody who’s customer facing to be involved usually, because it’s going to be a change to their process. Any kind of cross functional areas that are impacted, you need, as well as HR.

You need to make sure that you’re talking to HR because when you’re setting those program level milestones, sure, the technology may be ready in a quarter. That just means you’re delivering something, technologically speaking. You’ve still got to assess the life cycle. You’ve still got to assess the impact.

Chances are, if you’re doing something amazing in a quarter you’re not going to have everybody’s needs met. So maybe this is going to work for sales quarter one and then it’s going to work for customer success quarter two. Those kinds of things and the life cycle is going to kick in around quarter three.

So we take the time that we can to build in those learning milestones and those skill development milestones. And this is where you have an opportunity to build stronger across team collaboration, because oftentimes, of course, you’re building with an idea in mind. And of course, you really don’t know what you need until you deliver it and then find out what you didn’t get.

This is where you have those opportunity to have user group conversations to have facilitated sessions to have walkthroughs to be building those relationships with the people who are impacted by the change and the people that are literally building the technology for the change.

So it’s an opportunity to get everybody closer together and being on the same page. You know what? That’s a really great idea, but we can’t do that until this is done. So you’re building out those roadmaps to communicate. Here’s what we can deliver when and you need to build in those maintenance life cycles and those skill development life cycles as you go, because the leadership folks need to understand, yes, we may have blown through whatever we needed to do in terms of our own personal sleep, our own breaks, whatever, to hit this milestone. But now we need to understand what are we doing with our tech debt? How are we investing in the next iteration of this?

What are all the corners that we maybe needed to cut to get to this level? And then how do we improve that as we go? So understanding that building out the. Understanding of the team, the technological capabilities of the team, the skills of the team is required to make sure that you’re increasing velocity.

It’s going to go very slow at the beginning because it’s very new with everybody. But this is where, if we’re really doing agile properly, if we’re really thinking about the customer experience, if we’re really thinking about the employee experience, this is stuff that needs to be built in from the beginning as we go to level set those expectations.

Russel Lolacher: But Tara, one more goddamn change. My goodness. We’re already going through COVID changes and work from home changes. And then, and then to throw digital transformation on the pile when so many people are going through so much stuff outside of work, inside of work, personally, professionally, should timing not be taken into consideration or is it just, "Nope, sorry. We’re transforming now because that’s how technology works."

Tara Wilson: That’s a good question. So I would say two things. I keep, I always go back to compete or die. But I also think about if you can’t keep your business alive, obviously you can’t compete, but you can only go as fast as like traffic. You can only go as fast as the slowest person in your lane.

So what, so then that kind of begs the question of how do we build resilient workforces, right? How do we make people interested in change, wanting to keep up with what’s going on in the industry, feeling comfortable about making changes. And I think to your point, Oh, my gosh, it’s just been such a… dealing with COVID, dealing with lockdowns, dealing with all the mental health issues around that has just been jarring to say the least people. Are exhausted with it.

One of the things that that I’ve seen help a little bit is to have those kinds of conversations. I just, we just had an onsite planning session and people were like, wow, you’re shorter than I thought. Or, Oh, it’s nice to see your full view. Oh my God, you’re pregnant because you’re used to seeing just a face and, and so it’s, it’s getting back to the, "hey, remember when…" I call it the new BC, right? So now it’s before COVID. So it is important to go back and honestly, it’s those relationships that help. Hey, it was so great meeting you and working in the office. So taking that pause to just say, okay, as a human being, what do you need? So there’s, there’s strength in numbers and there’s strength in having those kinds of conversations to say, you know what, guys, I’m just done. I’m tapped out. I need you to run with a ball. I’ll, I’ll try to get my head around this. I’ll participate as I can. You need, it will go slower, but this is where you do need to give people time to just breathe again and just understand, okay, we can do this together. Maybe I can’t do this all myself, but I’ve got a team. I’ve got a team that we can work with. I can raise these conversations. I can raise these issues and together we can figure out what’s a good plan to go with. And I know shareholders don’t want to hear that, but at the end of the day, I can give you some bullshit date and say, yeah, sure. We’ll do it by this date.

And. We won’t make it. We’ll, we’ll cut scope. We’ll do the very bare minimum. You won’t be happy and we won’t be happy. So the one thing I hope that COVID brought us is a better understanding of work life balance because honestly, what are we killing ourselves for?

Russel Lolacher: Where are we getting this wrong? And I’m looking at this from both standpoints, not, I’m looking at it from different levels, actually. We’ve got executive, I’ve got change agents, and then I’ve got those being transformed, where is the disconnect that if it was removed or thought differently, digital transformation might be a little easier of a process.

Tara Wilson: I think honestly, senior leaders need to listen to the change agents more. And change agents need to make sure that they’re listening to people on the floor more, right? So my job as a change agent is to keep that pulse. What’s going on? How are people feeling? What issues are they bringing up? What things are they looking forward to, right?

You need to make sure that you’re building wins into whatever you’re doing. So you’re building that groundswell of excitement versus anxiety about the change. And this is where, if we’re feeding that information back to executives. The way we should be, there should be an appreciation for wow, I know we’ve only moved the needle a notch, but that was a big notch and that’s the first notch in the rest of it.

And this is where we need to celebrate those successes. There needs to be an appreciation from the people at the top. To understand what the rest of us are going through as we’re changing all of these things, because CEOs are great. They’ve got great vision, great understanding of where they need to be, great kind of laser focus as to, I want to be there, but it’s the rest of us that make it happen.

So the devil is always in the details. And this is where, okay, yes, on paper things look pretty simple. Five steps were there, but each of those five steps has 20 sub steps and some of those have different options around them. So yes, it’s going to take us a little bit of time. And this is why it’s so important to be the face of that change from an executive perspective.

It’s so important to make sure that you’re checking in with people just randomly over communication can’t happen. It can’t happen. So this is where a lot of times you’ll see skip level conversations being totally successful. You’ll see impromptu off sites. You’ll see anything that we can do just to make sure that there’s more of a comfortability level and having these conversations as opposed to a formal readout.

Here’s my status, right? Because those are all polished. Those are all walk through 75 times whitewashed. It’s okay, but here’s the real deal. People need to hear the real deal. And this is where it’s, it’s, it’s again, that shift from going from that, that waterfall capitalized mentality of we will hit this in six months versus we’ll get close in six months. We’re going to work on this. And as we go, priorities may shift what we want to accomplish as our first release may shift. The market may shift, so let’s pivot to that as we’re going. So this is where when you have it a little bit more real time, that’s exactly it. You’re not going to be able to say on June 1st, this is going to happen.

You’re gonna say, okay, in the next couple of months, this is what we’re working towards and we’re making solid progress.

Russel Lolacher: You slipped in the word vision in there. And I’ve always found that interesting as a communication tool, as also a buy in tool and also something you can get in the way. So how does a vision and a mission help with digital transformation for the employees?

Tara Wilson: I hope that if you’re having conversations with the right folks, if you’re having real conversations about the vision of where you currently are and where you want to get to the mission of how you’re trying to grow your business and what problems you’re trying to solve. Who your target markets are aligned with your values. You’re helping empower people to say, listen, I don’t know the right answer, but I know as I’m doing my daily job, this is directionally correct to get there. So what I try to do in delivering like new products, new services. Because they’re new, we’ve never done them before. So yes, we don’t have all the answers, but I can say every time I’m given a choice or an option or some kind of contingency that comes up that was unexpected, is this directionally correct?

Is this in the right area we want to go to attain this market, to be able to deliver faster, to hit the right goals that we’ve set as a corporation? If I can answer yes to those things, I keep doing them. Now I’m also not the kind of person who looks for permission. So it works for me, but when I’m working with a lot of introverts who are a little bit more concrete on how they like to deliver things. It’s a challenge. And so that’s where I always advise teams talk about this stuff. You need to build trust within your teams to say, I’m not sure if I should be doing this. I had a conversation just yesterday with some folks to say we don’t have approval to be working on this, but this person needs a lot of help. And they’re one individual. And I think we can make a really good success story out of this. I said, okay, go. Absolutely. If you’re helping one person, that’s one person who’s now going to become someone who gets it. Someone who will talk to other people to try and help them understand it and try to help build that groundswell of what we need to do and point to this team to say they can help you.

So this is where we’re helping each other. We’re not waiting for leadership to say, yes, thou shalt. We’re trying to be directionally correct saying, well, this is what we’re here to do. Let’s figure it out as we go. And really, I think it takes, it takes that a little bit of confidence to say, I don’t really get the vision, but I get it and I’m going to keep going until someone tells me to stop.

So you’ve got to be a little bit of a pioneer. You’ve got to be curious and you’ve got to just have faith that you won’t get your hands slapped if, and when you go a little too far. So again, that comes back to the leadership, making sure they’re supporting the right things.

Russel Lolacher: And psychological safety being so vital to that change because people should be able to try and fail and speak truth to power because transformation can’t happen in a vacuum.

Tara Wilson: Yeah.

Russel Lolacher: I have a question about those making the change though, because cursive knowledge tends to come up a bit when I’ve seen transformation.

And I say, this is someone who started in a very technical organization once and literally had a rule of "no acronyms for the first year." Like I don’t want to hear a single acronym from a single person because I’m new. I’m still learning. Don’t make assumptions.

Tara Wilson: Yeah.

Russel Lolacher: Change agents make a lot of assumptions, especially those drinking the Kool Aid of digital transformation.

We know we’re on the right side of change. We know this change needs to happen. So they’re very excited, but then that’s where that language comes in of digital, digital, digital, uh, innovation, innovation, innovation. So how, how would you say to somebody who is knee deep in language that others don’t understand, but they keep wanting to use that language without bringing everybody else with them?

How do you help that person?

Tara Wilson: So I think this is where the beauty of being a change agent is that you wear many hats and hopefully your personal philosophy is that of servant leadership because it’s your personal job to get a change executed. So you need to make sure that you’re communicating what needs to be communicated up.

You’re managing up properly, but you’re serving the people that you’re working with. You’re serving the people who are actually doing the change. So it’s very important to connect with them. I don’t know, public speaking 101, connect with your audience, right? If you’re alienating them. Literally, you’re alienating them.

There is nothing that can be done from that. You’re creating a barrier. So what you need to make sure is, I will actually ask people when I’m having conversations about things or talking to different teams. How did that go? What do you think? You need to have that constant feedback loop. Was there anything that I said that was abrasive to this organization?

Because sometimes it can change department to department. We don’t use that phrase here. Okay, great. Now I know, my apologies and you you can go and I would apologize Sorry folks, you know in my lexicon. This is what this means. Here’s what I’m trying to communicate so one you may temporarily look like a bit of an idiot, but I think you build stronger relationships because you admit, hey, there’s something I didn’t know and look, I’m still here. It’s okay. So you’re modeling that behavior to say, this is the way we need to be doing things. So I think it’s very important to make sure that not only are you talking the language that is common to the people that you’re talking to, but then when you’re managing up, you’re also advising of that.

You know what? You’re losing them. We, we need to have some messaging around this. And similar to this conversation, I’ve suggested things like we do a open house with, let’s talk to the CIO, tell me about your vision. Can you break that down? Because I now know how the rest of the teams are hearing this.

So when they go through their change speak, I can say "Okay. Can you define that a little bit more? Can you break that down for me? Can you say that in another way?" And it may be a little annoying to them, but they get it. And I also have these kinds of coaching conversations to say, listen, when you lose your audience, that’s exactly it. You’re putting a wall between you and them. We can’t afford that. If you want true transparency, you need to speak in a way that will actually resonate with folks.

Russel Lolacher: CIO stands for chief information officer for those playing acronym game at home.

Tara Wilson: Apologies. Yes.

Russel Lolacher: I’m like, I like, I like the first time I bring up acronyms, you sneak it into the answer. I’m like, Oh, perfect. I can’t not call that out.

Tara Wilson: Fair enough. Fair enough.

Russel Lolacher: So where do you start? You don’t know if your organization’s ready for this change. You don’t know if they’re ready for the scope of the type of changes being asked of them. You don’t know if their workplace culture is even on board with any of this. Where do you start?

Tara Wilson: Well, I always figure the leadership team has paid the big bucks because they have to take accountability for a lot of stuff. So I start with them and I literally survey them independently and I get them to rate things. How would you say your culture is? Is it open? Is it closed? How resilient to change are they?

How important is this initiative? How would they rate this, the importance of this initiative what department departments do you think are on board? What do you think is not on board? Is there anything that you see as a roadblock? But I literally like I go through a questionnaire and then I literally analyze and assess the, the change versatility rating. Okay. Here’s where I think we’re gonna have problems. And then I go one layer down and then I go one layer down. So I’ll have at least a good chunk of that conversation before I start anything. And then I will go back and say, I’m not sure if you’re ready. You wanted to start at point a, which is start the change.

And I think we need to start at, minus three. Let’s talk about why we’re doing this. Let’s talk about who needs to be involved. Let’s raise some concerns around what is this going to mean? What happens with in flight stuff? Is this more of a priority? How am I going to do my day job? Can I volunteer to be working on this?

So have those precursor conversations to start getting alignment on things to start opening that culture, because that’s exactly it. I keep telling people, if you spend a million bucks to build a Ferrari but nobody wants to use it and it just sits in the garage. What a waste of money, effort, and time.

So in order for you to be successful with this initiative, sorry, you’ve got to do some pre work and say, are there any mechanics out there? Oh, you like to work on, I don’t know. I shouldn’t have used the car analogy… transmissions? You like to work on engines. Okay, cool. Let’s build a team. But this is where you need to gauge that because change cannot be imposed, it must be worked through, if you really want it to work.

Russel Lolacher: I can’t tell you how many surveys I’ve seen recently about what executive thinks and what employees know. So there’s such a gap and it seems to be growing all the time about, Oh, this is our culture. And the employees are like, that is not our culture.

Tara Wilson: hmm.

Russel Lolacher: So if you’re approaching it with executives, And they’re telling you one thing, is that enough? Because it’s, you’re only getting one picture.

Tara Wilson: No. And that’s exactly it, right? This is where you bring it back and say, Okay, so here’s what you think here’s the, here’s the fantasy, here’s the reality. And that’s why we need to bridge this, that’s why we need to go back to minus three and start here. Because maybe in your mind, you think, even, oftentimes, you think that you have alignment in senior leadership. Guess what? You don’t. I always say it’s like, it’s like navigating a ship. If you start off and you’re one degree off, that’s the difference between hitting Australia and Africa. So you need to make sure that your senior team is aligned. Because if they’re not aligned, how the hell are people on the floor going to be aligned?

So this is where bringing that information back allows them to have those conversations. And I’ve had times where, no, no, no, it’s fine, just go. Okay, here are the risks. Here’s… I don’t want to say foreshadowing, but here’s what I think we’re up against. And then I will say, okay, be aware of this. We’re probably going to see this as it happens so we’ll need contingency plans for that. And so depending on the awakening, I think sometimes the leadership team needs, I will go hard and I will be like, okay, so when people don’t want to do this, what are we going to do. When people are uninterested? What are we going to do when no one shows up? What are we going to do?

Um I’ll, I’ll bring out different scenarios for them and just say, okay, how do you want to handle this? And honestly, sometimes I kill things because they’re not ready and no one’s ready to make a change. So there’s literally no point.

Russel Lolacher: So that’s the onboarding. That’s the pre work. How about the other end? How do you know you’re actually being successful at change?

Tara Wilson: I spend a lot of time doing one on ones. So if I, if I, I’ll, I’ll listen to, I’ll listen to team meetings. I’ll listen to things that are being said. I’ll listen to things that aren’t being said. I’ll see whether or not people are going on camera. I’ll see how engaged they are. And then I’ll start having different conversations with people.

I just asking how are things going? What are you doing? What do you think about this? So I try to build a lot of trust. I try to build a lot of open conversations and oftentimes people are just scared. They’re nervous. And I remember having a conversation with one person and she said if something happens that I don’t know what to do, I just call this person. Cause I don’t know how to handle this. I’m afraid of making a mistake. And I said, listen we’re working in retail, so worst case scenario, a price doesn’t get updated online. We, we have, we have a typo. We have a small issue, right? I said when 9/11 happened, the first thing that the mayor did was he went and he got a coffee and he sat for five minutes and he just sat there and said, okay how am I going to deal with this?

If all of these people were dying and all of this infrastructure was affected and there was an emergency that was cataclysmic in his, in his city. And he had the opportunity to take 5 minutes to think about how he’s going to strategize to do something. I think you can take a few minutes to think about stuff again.

We’re just talking about a website here. Again, it’s giving people permission to have that. What the hell do I do moment and. That person actually from that moment on started doing some of the training started saying, oh, this actually isn’t so hard started leading teams. And this was a 20 year veteran in something else who was one of those people. "I don’t think I want to learn this stuff." Okay, your call. But the other thing is, you have to give people the freedom to come to things on their own terms, because even if there are a few people in the department bought in, maybe not everybody’s bought in. So you have to make sure that you’re supporting those who aren’t and giving them the space to learn on their own time and accept stuff on their own time.

I mean, I know this is pie in the sky world, but honestly, if you want them to be effective at what they’re doing, that’s the only way you can do this. I would, I would say to people, take lessons from parenting, right? If that’s, that’s, it’s the same kind of mentality, right? Well, I’ll try it this way.

I’ll try it that way. I’ll try it that way. And oftentimes when you don’t say to your kid what do you want for dinner? You say, okay, do you want chicken or fish? Okay. Yeah, that’s right. So you’ll, you’ll find those ways of working that help, but you make it safe for them. You make it, you have to respond in a way that is where they’re at.

You need to meet your audience where they’re at in order for them to feel like they can, they’re empowered to make change and be part of the process.

Russel Lolacher: Do you find it interesting as a consultant versus an in house change agent, because you’ll have a lot of people that are consultants and the organization will be like, you’re not one of us. You’re not, you don’t know our problems. You don’t know our culture. Well, versus an in house change agent where they’re like, they’re part of the problem.

They have been part of the culture that has not transformed in a lot period of time. So how does that… How does that get covered as someone from the outside looking in?

Tara Wilson: I, again, I focus a lot on leadership because they’re the ones building this environment. They’re the ones building this culture, right? And oftentimes I need to remind them that if I’m an internal change agent, I report to somebody. I need that person to approve my salary increases, my bonuses, whatever.

It may not be in my best interest to point out a lot of errors in the ways that those people are doing things. I’m there as the third party to say, "You may want to look at these areas. These are things that are not going to be not going to execute well for you." So a lot of times, honestly, all that does is is identify some of the alignment or the misalignment.

I should say in some of those areas, and it helps break down those silos because they are doing the best that they can. Oftentimes I’ll have conversations one on one with those change agents. Hey, have you tried this? Have you tried that? Of course I did. Tried that six months ago. I tried, they tried that they did try to do all the right things, but they’re institutionalized and they’ve said, listen, I’m not banging my head against that wall anymore.

Like I’ve got a migraine. I’ll stay in my little corner. I’ll do what I can. And when you have all of the change agents on a major program thinking that that is a recipe for disaster, because no one’s taking on that bigger picture. No one’s taking this on cross functionally to say, okay, this is not going to hold together folks.

So oftentimes I’ll come in and point that out and say, okay, well, that’s great. But again, all of these cross functional processes need to change. So these people need to work together. And if no one’s able to actually raise the right issues, This is not going to be successful. You’re setting people up for failure.

And oftentimes, if you can say something like that, then you’ll wait a minute. Okay. Now I think I need to act.

Russel Lolacher: Somebody’s listening to this going. This is a lot of work. This is, this is, there’s too many spinning plates. I’ll use another car metaphor. So no, neither one of us understands it. Something along the lines where it is very much about. Uh, it feels like an overwhelm. So I guess I want to tackle something you mentioned at the top, which is digital transformation could be many different things.

Do we need to go through a process like this for every type of digital transformation? Is there a threshold going, okay, you cross this line. So now it’s a huge moving an iceberg versus it’s just using PDF now. It’s just a smaller change.

Tara Wilson: Yeah.

Russel Lolacher: Is there a scope or a range when it comes to this kind of work?

Tara Wilson: I would say there’s a relative response. So something that’s going to be cross functional, like we’re going to fundamentally change our website. So all of the lines of business now will be represented in our website. Uh, and we, this is a big initiative we want to undertake. I would say, okay, start now and bring in all of those pieces because you need to be able to assess the magnitude of that change, right?

As opposed to, okay, everybody, we’re going to go from one documentation system to another documentation system. Okay, cool. You still want to have all of the people that are impacted have that conversation. But the magnitude of that impact is going to be smaller, right? So this is where I would say the approach needs to be the same all the time.

Who is impacted by this change? What do they need to know? Who do we need to align on buy in for this change? Who are going to be the people that are going to be advocating for this change, or at least responsible for being that conduit between all of the groups to say, Hey, we’ve got a problem over here.

We’ve got a problem over there. Let’s work this out. That needs to happen regardless, the amount of time it takes to pull that stuff together is also relative. So the bigger the change, the more you need to be talking about the impacts of it before you start anything so that you can make sure you’re, you’re starting off on the right foot.

You’re setting, you’re, you’re charting your course properly because if you miss a couple of people in that, in that initial push, if you will, you may have to. Have a hard turn somewhere where it’s very costly. It’s not time effective. It’s going to cause some relationship issues because people have been going in one direction and now they need to totally pivot.

So you need to make sure that that maybe this is the project manager and me, but you need to make sure that you’re starting off on the right foot to plan for the right things in order to get the outcome that you want. And it, while it is a lot, that’s why you plan this, this kind of stuff. So you can say, okay, for the next three months, I’m focusing on just this.

Just this piece and then we’ll go forward. And as you’re doing that, I always look for people who are interested in learning more, doing more and who will support it, because it’s a lot of work for one person. When you start enabling agents in all the other areas, it’s a lot less work. And that’s what helps support the change through doing, not being told.

Russel Lolacher: I think I got to wrap it up with the big question at the end, Tara. Thank you so much for talking about this. I could keep talking, but I know podcasts do have to end eventually. No, it’s all good. What’s one simple action people can do right now to improve their relationships at work?

Tara Wilson: I love this one. Okay. I would say understand that what is common sense to you may not be common sense to the person that you’re talking to. You might have had weeks, months, whatever to think through what you’re trying to accomplish. And this person may be hearing it for the first time. So to your point earlier, don’t make any assumptions.

Talk it’s, it’s old school, but who, what, when, where, why, how all of those things make sure that as you’re talking to people, you’re covering those bases. So they get an understanding of the context. One of the things that always happens to me is no context. Hey, can you do this? Sure. Why? How can I do a good job if I don’t know why I’m doing something? I don’t know what the point is. So always make sure that you’re, to build a relationship, you’re, you’re pulling people in, as opposed to pushing stuff to them. That’s what I would say.

Russel Lolacher: That’s Tara Wilson. She’s a speaker, executive coach, director of client partnership at Rangle.Io and a digital transformation consultant. Thanks so much for being here.

Tara Wilson: Thank you.

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