Managing Stakeholder Perception: How Product Leaders Build—and Lose—Influence

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Hannah Clark: Most of us spend years climbing the corporate ladder only to realize that the keys to the corner office don’t necessarily come with the keys to the hearts and minds of your team. So we brought together two executive coaches who have seen it all — Carolyn Dolezal, COO at Americas’ SAP Users’ Group, and Kate Leto, who’s coach senior teams at JP Morgan Chase, The Financial Times, and more.

They joined us for a candid panel discussion about the myths, realities, and challenges of executive leadership, and specifically the ways leaders can gain the confidence and trust of internal and external stakeholders. You’ll hear their unfiltered insights on why your personal agenda might be sabotaging your C-suite team, how to build influence when the odds are stacked against you, and the art of recovering from early leadership mistakes.

Whether you’re already in the C-suite or making your way there, these tactics will impact the way you lead starting today. Let’s jump in.

Oh, by the way, we hold conversations like this every week, so if this sounds interesting to you, why not subscribe? Okay. Now let’s jump in.

Without further ado, I’ll introduce our guests today.

So first up, we’ve got Carolyn Dolezal. She is the COO at Americas’ SAP Users’ Group, or ASUG, and an executive coach dedicated to developing high performing leaders. She’s got a background in operations and organizational strategy, and she helps teams scale sustainably while empowering individuals to lead with clarity, confidence, and impact.

So Carolyn, thank you for joining us today.

Carolyn Dolezal: Thank you. Glad to be here.

Hannah Clark: I’ll toss a little jeopardy question to you to get us acquainted. Carolyn, as someone who’s coached execs and run ops yourself at scale, you have seen a few things. What’s something that’s commonly touted as a leadership best practice that you think is, it maybe makes you roll your eyes a little bit?

Carolyn Dolezal: One of the ones I can think of, and it’s some advice that was given to me initially as I was entering, is never let ’em see you sweat, lead with an iron fist, and kind of goad people to their best performance. I think there’s some merit to setting high standards and encouraging people to get to the best performance, but acting like a field marshal, I don’t think is effective.

Hannah Clark: Great. Thank you for joining us.

Next, we have Kate Leto. Kate has been immersed in product management, organizational design, and personal development for 25 years, and she’s an accredited executive coach. She’s worked with senior teams and individuals at JP Morgan Chase, The Financial Times, Comic Relief, TUI, The Boeing Company, Merck, and many more.

Kate, thank you for joining us.

Kate Leto: Thank you. Very happy to be here.

Hannah Clark: So Kate, you’ve led some teams as a product leader, and now you coach top execs across many different industries. So what’s one belief about leadership that you have held onto that coaching has changed your perspective on?

Kate Leto: Yeah, I’d say the biggest, strongest belief that I had when I entered my first product leadership role was that I had to have all the answers right.

I had to know exactly what we needed to do. I had to be able to fix any kind of challenge that my team or the organization was walking into, but it was all on me. I needed to be the hero, like every day. And as a coach, I see how harmful that is not only on, the individual who, if they’re actually trying to do that is, is going to face some challenges in wellness and health and mentally as well.

Just being able to kind of power through, but also to the organization. Because if you’ve got, if you’re this leader who handles everyone’s challenges and problems, you’re not letting people grow. You’re not letting people handle their own challenges and take on those for themselves. So I’d say that’s the biggest mind shift I’ve had going from product leader to coach.

Hannah Clark: So today’s session, we’ll be focusing on managing stakeholder perception, how product leaders build and lose influence. We’ll be talking about this topic in three sections. Section one will be the fact and fiction of executive leadership. We’ll go through some myths versus reality and some best practices in that way.

Then we’ll focus in our second section on navigating external stakeholder relationships. Then on our final third section, we will talk about working with internal stakeholders, which I’m sure is what everyone is very focused on. Then towards end, like I said, we’ll be doing a Q&A.

And without further ado, our first question under fact and fiction of executive leadership, what are the most common, unintentional missteps that leaders make as they transition into an executive leadership position?

Kate, did you wanna take this one from the top?

Kate Leto: Sure. I think building off of what I just was talking about in terms of what I learned personally going from being a product leader to being an executive coach is this idea that we have to as leader or executive or member of the C-Suite, that we know it all.

And that we have to be able to solve or that we can solve any challenge that’s coming our way. I’ve seen it referred to, and I often use with my clients the phrase strategic over functioning, right? Like that we think that we need to be able to handle it all and that we can handle it all. So I think that’s something that continues to stand out as a problem that we’re dealing with and the lead leaders as we kinda step into these roles.

It’s just that we put it on ourselves to be able to take charge and handle all of the problems and come up with all these great solutions. And I think it just puts us as leaders into a very awkward position from the get go. So I say that’s one of the biggest missteps that I’ve seen.

Hannah Clark: Carolyn, did you have anything you wanted to build onto that?

Carolyn Dolezal: I think as you enter into the leadership role, it is a little bit as Kate was talking about. It’s not a performance, it’s not performance art. There’s gotta be substance. And then how do you build your substance quickly? Because you don’t know all these things.

You don’t know all the answers. What I found is useful is if you have a process through which you’re gonna gather information about customer needs, stakeholder needs, staff needs. Articulate your process. Tell people how you’re going to come into this. You’re not coming on in day one with a lot of heavy pronouncements.

And then listen. Listen really hard and really ask those questions because you want to be able to make smart decisions and you can’t do that without data and information. And the best way to get data and information, I have found is to ask. Ask at various levels and ask in various pockets of interest.

Hannah Clark: Do you have anything to add, Kate?

Kate Leto: Just one other thought that I had about it is that, when we step into leadership roles, we’re often going to be modeling the leadership that we’ve seen before. Be it, you know that iron fist often is what we have in the back of our minds ’cause it’s the way that we were managed perhaps, and other roles in other organizations.

What I’ve noticed is that there’s this tendency to just adopt that style, right? And try to make it our own. And as we do that, we kind lose our own authenticity. We lose touch with who we are and our values and what our skills really are and in many ways what got us to that role.

So I think that’s another common misstep, is that we’re not taught how to be a leader and much, against kind of what some kind of common concepts are that I don’t think we’re born, I don’t think there are many born leaders either. I think it’s something that we learn and something that we grow.

It’s a developmental skill like anything else but in, in kind of the vacuum that we often step into as a new leader, or even moving up kind of the corporate ladder into the C-Suite. We still don’t really know what we’re doing, right? We’re making it up as we go along, and we do have that tendency to just grab onto what we’ve seen before and what we’ve experienced before.

Instead of really taking the time to have a good understanding and build our own self-awareness of okay, who are we and how do I wanna bring that into an organization and build relationships with my team, be it C-Suite team members, or folks that are part of my team and my organization. So I think that’s something else to be very aware of as, we’re stepping into it, be it our first leadership role or much higher up that ladder is.

Unless we do take some time to step back and think about what kind of, what does it mean to be a leader and how do I wanna bring that into my work every day? I think we do fall into that vacuum of just grabbing and adopting what we’ve seen before, and I think that’s really dangerous.

Hannah Clark: Good point. And I think that leads really well into our next question about pervasive and maybe unhelpful tropes about being in the C-suite that might maybe dissuade people from feeling that they have a position there or that they would fit with that kind of a culture.

Or that might be just setting people up for the wrong expectations in the role. So what would some of those more pervasive myths look like?

Carolyn, did you wanna take this one?

Carolyn Dolezal: I think one of the ones that I know I had thought was true and then encountered is as your added level in the organization, and you look upward, my tendency was to believe that these people were in those roles because they had things figured out and the alignment was there and this is what we were aspiring to be. And then sometimes even if the modeling of the behavior wasn’t exactly what I wanted, but that leadership seemed great. What I found when I actually entered the room is not everybody in that room, even though we’re called the leadership team or the executive team, not everybody’s agenda and not everybody’s goals are necessarily aligned.

And I assume that’s established there and then cascaded. And that’s how we, at our earlier levels, understood what to do next. But it caught me by surprise. There are private gendas, there are functional agendas, there are, real estate grab agendas that kind of happen through things. So just assuming that because you’re on the team that the team has common interests is something that you wanna examine and test those assumptions, and it does come from the top.

And then likewise you for your team, et cetera, to just keep reinforcing that ’cause things do shift, things drift. And then people are humans, they have their own agenda sometimes. Not everybody is aligned even though you think they should be.

Hannah Clark: Kate, did you wanna add on that?

Kate Leto: To add on to that and to add on to what I was saying just a minute ago about some of the common missteps and the fact that we, leadership itself is something that we learn through practice and we learn through trying to focus on specific skills is that it’s we need to realize that just because they’re in the C-suite doesn’t mean that the personal development or that leadership development stops, or that the learning stops.

I think a lot of times we have that kind of impression in my, in our minds, that they’re in the C-Suite. They’re the CTO or the cmo, or the CEO. They must know everything that they need to know, right? They must be really good at their jobs and they’ve got it all up here. To Carolyn’s point that it doesn’t mean that the team is aligned by any means, but it also doesn’t mean that leader should stop growing, right?

Or can stop growing. That personal development comes to a halt the minute they step into the C-suite. That’s something that’s really important as well, because just because you’re an executive, it doesn’t mean you, you do stop growing, doesn’t mean you do stop learning. The best ones continue to evolve and continue to grow.

Carolyn Dolezal: And I think toward that is that, where do you as a leader get your feedback? Are you getting feedback? Are you listening with the intention of using that to continue to improve and grow? And I think what’s sometimes challenging is as you get to the higher levels, is who? Who will speak to the truth to you, who dares to speak the truth to you? Depending on how their experience with leadership is.

I don’t wanna tell ’em anything they don’t already wanna hear. That can be extremely damaging to the organization. So it takes trust, it takes a willingness to take that feedback in. Listen, and if there’s a mistake or an error or a shift, acknowledging it, that can be really powerful in an organization.

And the leader’s gotta be willing to take it on first. And I think asking for feedback versus hoping people wander in and offer it because they might do it to their own detriment. I think asking for feedback, listening carefully to it, and then acknowledging it and then saying to the organization, you’re gonna work on something really holds you accountable.

And I think that Who are your truth tellers and make sure that you access them often.

Kate Leto: Yeah. Building influence as an executive, I think one of the best ways you do that, as Carolyn is saying is asking for feedback, taking on board every other people’s opinions and perspectives on, whatever it might be.

A new project, a new hire, a new strategy, a new direction, and getting out into different areas of the organization and different levels. Not just always going to the person right below you for that feedback, right? Getting into the different areas and different levels of your organization to build those relationships and ensure you’re building that habit of feedback, of asking for feedback and actually, acknowledging it and taking it on board.

Yeah. I think it goes back to this idea that just because you’re an executive doesn’t mean that, that you don’t, that there’s not areas to improve, there’s not areas to grow, and there’s not areas that you can build relationships to get some really good feedback to help you do that.

Hannah Clark: Yeah, absolutely. And I, I think when you have those kinds of strong and established relationships, then people really believe and trust that you have their best interests at heart and that you’re representing, their voice in your decision, it’s strategic, but I think it’s also, it’s good business and it’s makes for a much more rewarding career when you have that kind of a a smooth working relationship.

Kate Leto: Yeah, it’s, it’s a sure way to grow influence for yourself and to be that model to others in the organization on how they can do it too.

Hannah Clark: We’ll move then into our next section. We shall be navigating external stakeholders. We’ll move right into our next question, which is, what are the most important habits, policies, and conversations that leaders should be having and committing to if they wanna build those solid relationships with external stakeholders?

I know we’ve just touched a little bit on some of those internal relationships. Kate, what would you say about some of the best practices for external relationship building?

Kate Leto: I think it’s a lot of the same stuff as internal relationship building. One of the things that I talk to clients quite a bit about is upfront, be it a new member of a team or a new external stakeholder, is to get really clear about what your expectations are of each other, and actually make some committed agreements around those.

And that could be anything from how you’re gonna communicate when times get tough. How you’re gonna talk about deadlines and timelines, how your, what your ways of working are going to be. Who’s responsible for what within the relationship. It’s actually having an ongoing conversation that you can check in on, what are your expectations of each other?

What are the agreements that you’re going to make and commit to, and make that just an ongoing part of your relationship.

Hannah Clark: And that’s very relevant ’cause it sounds like navigating competing priorities is a big challenge for external stakeholders. Does anyone wanna chime in on maybe some ways to manage some of those kinds of challenges?

Carolyn Dolezal: One of the things that I’ve found helpful, and I’ve been on both sides of, I’ve been a external stakeholder providing services and I’ve been a consumer of service. I find it easy to cut to the chase and just ask in an early stage conversations, what does success look like? What does success look like for the external stakeholder?

And then us sharing what we think success looks like. One of the things, for instance, as a customer and purchasing from or working with external stakeholders is I need them to be healthy. I need them to be viable. I need them to have, be profitable. And so we are interested in doing that. It’s not just all about price or that sort of thing, but it’s like how are we gonna deliver?

And how do we make it as smooth as possible? And I find that when we can both articulate, although what success looks like, sounds like such a simple question. It’s a, a Byzantine set of interwoven priorities. When you start to talk about it, it’s easier to refer back to that and then say, are we tracking to what success looks like?

And then having that communication cadence, the timing of it, setting up deliberate times to talk, not just about what’s happening and the outcomes, but how’s it going? Is the process working for us? I find that helps shortcut a lot of things that could wind up ballooning or festering if they’re not addressed in a timely basis, but getting the mutual expectation on what success looks like no matter what your plan is.

Something else always comes in sideways. How do we handle it when something shifts? And then being able to talk about it and appreciate and respect the other party and both views because we need both parties to get things done.

Hannah Clark: Okay, we’ll change a little bit of the pace again because I do wanna talk a little bit about personal branding and some of the ways to navigate sometimes there’s push and pull between one’s, establishing one’s personal brand and then navigating the brand of the organization that you represent. There’s also the matter of just, making sure that your personal brand continues to represent who you are. So what are some effective strategies for navigating just personal branding and the ways that it plays into your professional reputation?

Carolyn, did you wanna take this one?

Carolyn Dolezal: I think what is the public face that you put on, whether it’s public, internal to the team, or public to your external stakeholders and the marketplace. It’s having a really good sense and a strong understanding of what the organization’s brand is, and then for yourself, what is your brand, which is a promise of this is what you can expect from me when we have an interaction, and then looking for as much alignment as possible.

Some organizations expect you to be the public voice for the organization as if you’re the spokes model. Others let you be you and you’re a leader and you happen to be affiliated with this organization. So understand what the cultural expectations are. I know for instance, when I was working with public companies, you have to be very sensitive and aware of when are you talking as a private citizen and when are you talking or being perceived as being talking as part of that organization.

So be careful with that, and then within that being true to yourself. Because if for some reason the projection of the company isn’t aligned with who you are, that’s gonna grind on you over time. So as, as aligned as you can be, and hopefully there is a strong alignment, but over time, if you are misaligned, it’s. Might not be the best place for you.

Hannah Clark: Fair enough. Kate, did you have anything to add?

Kate Leto: I think it comes down to looking for areas that you’re gonna have some overlap with your company’s brand and focusing on those versus feeling like you have to be an echo, like an echo chamber of everything you’re saying and doing.

It comes back to, again, having a good understanding of what your own values are and how are showing up not just to work to every day, but within your community, right? And how, where there is some overlap between that and what your company is bringing on or what your company portrays with their brand.

And yeah, sometimes there’s a lot of tension there and especially, I’d say probably recently there and somewhere, oh yes, there might be more attention than before. And I think that’s pretty normal because, as, although we sometimes forget that organizations are made up of a lot of individuals, a lot of people, a lot of humans who all have have their own values, their own beliefs, their own experiences that they’re bringing on.

So I think it’d be quite rare for their not to be some kind of tension between that, a personal belief and the company belief. Hopefully there is that overlap though, and I think that’s what you focus on. And it, it’s not only representative of what you’re saying publicly, perhaps be on LinkedIn or whatever social platform that you use, but also how you’re representing yourself internally.

It’s showing up and how you’re making decisions and how you’re building relationships with your team members and your own managers and things like that. So a lot of it, I think just comes back to that core element of having good self-awareness and good understanding of your own values and your own beliefs.

And how you can bring them forward in a, and hopefully a positive and productive way.

Hannah Clark: And then that brings us to our third section, which is working with internal stakeholders. Probably the moment that many of us have been waiting for. We’ll get started with our first question of this section, which is, what are some of the most effective habits that leaders can build to inspire confidence and buy-in with their teams?

And I think we have touched on some of this before, but I’m sure that there’s plenty more that we haven’t gotten to.

Carolyn, if you wanted to take this one away.

Carolyn Dolezal: One of the things that I’ve observed that help build some of that confidence and buy-in with teams is transparency. As much transparency as possible, having the relationships with the others that you’re working with, because things change and the strength of the relationship and the trust factor there helps you weather a lot of storms.

It’s being very respectful of the other party’s time. Where do you need to dial them in? Where do you want that input? How is that input taken and treated? And I think just as you talk about the process, narrating it out loud so people know and understand what that is, but it’s doing what you say you’re gonna do.

Doing it and then reminding people that it’s been done and what’s next, I think is a really strong way to keep that faith and trust and smoothness running.

Hannah Clark: Kate, I’ll let you if you wanted to add anything about effective habits and inspiring confidence.

Kate Leto: Sure. Some of the things, you’re right, we have touched on, I mentioned that I think it’s important to build relationships at all areas of the organization.

I think that helps build confidence a lot because you are, the doing that I think was the 50% is showing up and is being seen by people throughout an organization, not just perhaps within your silo or within your team, and asking for feedback there. I think that’s a great kind of signal of the kind of leader you are the kind of leader you’re hoping to become.

But also I’d say one of the key things, and it’s interesting, one of my clients shared this with me, that what he really strives to do as a leader is to deliver. He feels that the biggest that the best kind of kindness comes from just being clear with messaging. Polarity is kindness, is what he said, and what always is in the back of my mind when I’m talking to new leaders who are coming into these roles perhaps for the first time.

So just being really clear on, again, who you are, what’s the direction you’re going in. To Carolyn’s point, being transparent, of course is a big part of that. Sharing that information, sharing the why behind the decisions that you’re making, but just being as clear as possible as you can and repeating it when you need to repeat it.

Honing in on the different kind of aspects of how this might impact each individual within your team and also the organization at large. Just really keeping in mind that having that clarity, being as clear as you possible is kind to everyone in the organization, and sometimes that means also the feedback that you’re giving to others.

So I think that’s a great thing to keep in mind as we’re thinking through how you can make influence more real and how you can bring it into kind of the doing aspect of your job.

Hannah Clark: So we’ll tell a little bit of stories about amazing leadership in action. Personally, I’m a big fan of learning through storytelling, so I’d love if if our panelists could share some stories of just some amazing moments of leadership that they feel have a part that we can really take home with us today.

Carolyn, did you want to share or start us off with a story of a leader that has impacted your own perception of what it means to be a great leader?

Carolyn Dolezal: I’d love to, and this is probably one of the best leaders I had the privilege to work with. He was an individual who came from like a sales background, so a gregarious, extroverted kind of individual.

I did like the operations and the back office stuff, and he was like the front guy. We had a really good push and pull in terms of how we wound up working together. But what really inspired me about him as a leader was he listened to and looked at key players in his team, and as Kate talked earlier, multiple layers in the organization.

So he knew his people, he understood his people, he saw what was their particular strength and understood interrelationships. And then if he saw something in somebody, he would open doors. He would make introductions, he would give assignments, he would make things happen, and years after, and I owe a lot of, I think my early successes to his style when I would thank him for it later, he was almost bemused and said, what?

He said, I didn’t do anything. You did all the work. And I said, you opened the door. The fact that you opened the door and knew I could walk through it, even if you said there’s a door, go ahead. That just, it changed everything for me. So I think his generosity in understanding who is gifted where and where that could be used next, and then creating an opportunity or at least an on-ramp, I found that to be remarkable and I’m really grateful for it.

Hannah Clark: Kate, do you have any stories that come to mind?

Kate Leto: Yeah, there’s one leader who very similar in some respects to the story that Carolyn just mentioned. He was the CEO of an organization that I went in to do some product consulting for a while. And what I really, he was just, he was very human, right?

He was very funny, he was very personable. He was very open. He loved learning new things. He always had another book, a new book he was reading and a conversation that he wanted to have based on that, to try to figure out how he could bring this into the organization if it made sense, and if it didn’t, he had great trust in the people that worked for him.

And you just felt like there was this really good kinship with him. Like I almost didn’t feel like he was the boss, the CEO. He was just somebody who was in your corner and wanted to help you figure out how you could be the best you could be at your job. He took risks on people that he thought were ready for them.

It’s always open to new ideas and new ways of thinking about things. He had no problem saying no when he needed to, that it just wasn’t the right thing. And he also, his decision making was very inclusive. He liked to bring people into the conversation. He did a great job at getting perspectives from people from all throughout the organization.

He had to know everybody within this large organization by name and he knew their backstory. As you can see me just going on and gushing about this guy, he was a great leader, and I don’t see many like that.

Hannah Clark: Do either of you have more stories you wanna share before we move on?

Carolyn Dolezal: I had a quick one I can maybe share.

I had the opportunity to attend a executive club meeting last night here in Chicago and the guest speaker was Melinda French Gates. And so I’m sharing a Melinda story, but she talked about how initially in her work life she was in a culture that was aggressive and very competitive and a lot of sharp elbow throwing and felt that.

Wasn’t sure it suited her, but she said before she chose to be in another environment. Let me bring myself, so this goes back to the authentic self. And she had high standards, communicated that to her team and said, you’ll prepare for the presentation. I will work with you to prepare, you’ll give the presentation to the group that’s reviewing it, and you’ve got my support.

I’ve got your back. And she found over time when she was truer to herself and did more of that supportive kind of leadership, that it became a talent magnet. She was able to attract key talent from other places in the organization. They were saying, how did you ever get that guy to sign up with your part of the organization?

And she said, I don’t know. Maybe he just wanted to be in a place where he felt supported. I listened to that and I heard she had a 1800 person division, I think at that time, that she was leading the notion of providing support. Providing the opportunity, having the high standards holding it, but then also helping people adhere to it.

I thought that was something I just admired about her style for a long time.

Hannah Clark: So inspirational. A huge thanks in advance before we get to Q&A to our panelists. So Carolyn, Kate, thank you so much for making time in your days to be with us.

Kate, I know that you’re quite a bit ahead of us time zone wise, so we really appreciate you making the time. If you’d like to connect with Carolyn, you can connect with her directly on LinkedIn and then Kate as well. You can find her on LinkedIn or you can check out our website. There’s kateleto.com, which has her coaching courses and many other resources available.

Alright, and without further ado, our final section, which is going to be just questions from you folks.

I’ll start with a question from Galen. He says a lot of my executive leadership examples have been Caucasian male leaders. The way I saw them build their influence isn’t quite viable for me as a visible minority. What are some of the strategies that minority leaders can use to play the game when the rules are different for each player?

Carolyn Dolezal: I’ll offer perhaps to start. I think the it goes back to the audience that you’re playing to and when you’re playing to that C-suite, it is tough. It is a challenge. I had a mentor tell me at one point that if you aren’t cut from that same cookie cutter mold that they are, you may have to be twice as good and you may have to work twice as hard before they believe it, not see it, but believe it, that you’re able to do it sustainably.

That was the reality of the situation I was in and instead of finding it really disheartening, I actually found it encouraging is at least I knew that there’s potentially this breakthrough. But it was needing to be good. It was needing to do these communications and it was needing to be persistent and to determine if that’s what I wanted to do, stay true to myself.

There’s a lot of overlap. I think, or I hope a certain amount to get and be able to deliver there. There are things that are different. I have been working for many decades now. I still don’t have all the edges rounded off, but at least I can feel good about what I’m doing. But I understand it is probably harder because not everybody in that audience wants to believe it is possible.

Hannah Clark: This next one is from Agueda. This is about revisiting agreements. They say during the life cycles of projects, there are inflection moments where agreements need to be revisited. How do you maintain the momentum of the project while revisiting the agreement with stakeholders. They add, this could lead to a wrong outcome of a project or a missed agreement, or what happens when the revisited agreement leads to the need to create a different outcome of the project.

So a bit of more of a complex question. Does anyone wanna take this one on?

Kate Leto: Things are always gonna change, right? So I think that’s a foundational belief or something that we need to accept is that, the world changes a million times a day.

So of course things are going to change in your long-term relationship with the stakeholder, and it’s gonna be challenging and it’s gonna be frustrating at times. I think one of the best things to do is to, in those initial upfront agreements that you set up. How are we gonna check in when things go off the rails a bit.

And for a lot of, with a lot of my clients, larger organizations, we put in place some, a different kind of adaptive practices, make sure that you have retros with your stakeholder or with your external stakeholder, every quarter or something like that at a cadence that you feel is the right way to go.

So this becomes like a natural habit, a natural way of working. You’re always going to have this kind of conversation maybe once a quarter, a couple times a year, whatever it might fit for you. I think in terms of motivation, I’ve seen where these kind of conversations really go off the rails when we’re just doing the same type of conversation every time, you’re reporting certain numbers, you’re checking in on certain things.

There’s really no opportunity to actually have some different conversations around what’s working with the relationship and what’s not. What kind of changes do you need to make and how you’re working together, and really get into some of those more juicy or meatier things versus just checking dates, checking timelines, perhaps checking, personnel that you might have working on different projects.

And one, just acknowledge the fact that you need to have these conversations. They’re really important to have set up a cadence upfront that you’re going to stick to and change the tone of those conversations from time to time when you can to make it more about how are we working together, what’s going well, what’s not going well, and what do we wanna continue to change versus perhaps a template in check-in, which I often see happen between client and stakeholder.

Hannah Clark: Thank you for that. That was a great answer, Kate.

I wanna move on to this question from Amelia, which I think is one that probably all of us have had to ask at one point. I feel I’ve lost stakeholder influence early on by making a lot of mistakes. What can I do to build my influence back up?

Carolyn Dolezal: That’s a good question.

Maybe some suggestions are, I find acknowledgement of what might have not been delivered the way I had intended or wanted it to be, where it’s appropriate, an apology and a remedy. And so this is what we will do. And then I think the kind of re it takes time to rebuild trust and it takes time for people to believe it’s different this time.

So it’s unfortunate, but I think it’s solvable, but reestablishing what it is, how this works, being respectful of their time. But carrying forth over time, they’ll remember maybe the more recent experience and they’ll forget the initial experience. It just takes a while to dig outta that, that hole.

Kate Leto: Yeah. I had a client ask me this question this week. It was really interesting. Some, she’s working rebuilding some relationships within her organization and I think, first off, it’s just letting people know that you’re working on it. Carolyn’s point about acknowledging it. This is something I’m working on.

Some feedback that she received, acknowledging the feedback. Tell them you’re working on it, and check in with them again to see how things are going to see if they’ve noticed a change. That maybe is not a conversation you can have with everyone, but I think there are probably a few people within an organization that you can.

Carolyn Dolezal: I’ll also say it’s not comfortable, and that’s okay. It’s not gonna be comfortable. There’s no, I don’t have a silver bullet or a smooth way, but I think with the perseverance, you can turn things around.

Hannah Clark: Yeah, I think that, that show of good faith is very powerful and just, leveling with people that you’re aware of the concerns and that it’s a signal to be attentive and invitation for further and very honest feedback. So I, yeah, I appreciate that answer as well.

Our last question is from Yaron. What are some strategies that we can use to mitigate some of those challenges with regards to communication throughout the org chart?

Carolyn Dolezal: Couple of things. I think there’s quantitative ways to gather feedback, and I know that’s really popular and you can get numbers, but I personally find that qualitative feedback is really helpful because you can go deeper and get richer and some nuances that you might not have otherwise thought about.

So offering some space for that. And this is, I don’t know, it’s, maybe it’s my Midwestern, middle class upbringing. But if there’s a way to share a meal with somebody or like host a breakfast thing or, and I find smaller groups, people are sometimes feel freer to talk in smaller groups than if they’re in a big group.

Somehow there’s a dinnertime diplomacy. If you can talk over food, I think that helps. And then leaving that space and then do not under any circumstance, act rushed. If you allow half an hour for the conversation, don’t block anything on your calendar after that because you don’t wanna be like, okay, hurry up and then let me get outta here ’cause then people will withdraw.

Those are some things I think that are helpful to get some depth, to understand what’s on their mind. And usually it’s the last two minutes where you hear what they’re really thinking. The rest of it’s preamble and warm up, but in the last two minutes they’ll deliver the payload of information you’re looking for.

Hannah Clark: I love this tip. Thank you again to our panelists, Kate and Carolyn. This is wonderful to have you here and I really appreciate the gift of your insights that you shared with us today.

Kate Leto: Thank you.

Hannah Clark: Thanks for listening in. For more great insights, how-to guides and tool reviews, subscribe to our newsletter at theproductmanager.com/subscribe. You can hear more conversations like this by subscribing to the Product Manager wherever you get your podcasts.