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How to Evaluate your Executives

How to Evaluate your Executives

A conversation with CEO coach David Lesser

Founders often ask me how to up-level their leadership teams. Their questions might include:

  • My director of [function X] was one of our first employees. How do I help them grow into a VP?

  • How do I know if they are actually ready to be an executive?

  • How do I set expectations with them?

I had these questions and more when we were experiencing hypergrowth at Gainsight. I didn’t want to replace my direct reports if I could help it. I wanted to help them grow their skills as fast as the company’s requirements were changing. So I teamed up with a stellar executive coach to create a framework for what it means to be a strong executive. 

David Lesser is a leadership coach, but more than that, he’s a philosophical guru. I worked with him for several years at Gainsight. His focus is on helping CEOs and executives with self-actualization, which he strongly believes makes them better leaders. 

In this episode, David and I discussed:

  • Why is it important to set expectations for executives, apart from the targets on your metrics dashboard or the requirements in their job description?

  • What are the 4 competencies that executives should demonstrate?

  • Why is there no universal definition of a stellar VP of Sales?

You can listen to the podcast or else read the lightly edited transcript of the conversation below. If you scroll way to the bottom of this post, you’ll see the actual guide that I used for coaching my executives at Gainsight.

I always love conversations with David, and you’ll see why once you listen to this episode. Enjoy!

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Allison: David, I'm so excited to have you on the podcast today. Thank you so much for joining us.

David: Yes, my pleasure.

A: We go way back.

D: We do.

A: We started working together back when I was a couple years in at Gainsight. I'm so grateful for all the things that I've learned from you over the years as an executive coach and as a leadership coach. I'm really excited to share with the audience some of the things that you've taught me along the way.

D: Well, thank you. And I learned most of what I learned from my clients. It's been a two-way street.

A: This will be a special conversation. We are here today to talk about executive competencies and what makes a great executive. Often, when CEOs think about what makes a great executive, their mind goes to the job description that they usually post when they're recruiting for a role—whether it's their first VP of sales, their first VP of marketing.

Obviously, job descriptions are important. They help you evaluate candidates and set the initial expectations when someone joins a company. But job descriptions are quickly forgotten, and there are probably other reasons why a job description is insufficient for setting expectations for your executives. Why is that?

D: What you're looking for is to grow people and to have a growth mindset. You don't just want people to do more stuff, you want them to grow their capacity. If you have people with more capacity, you as a leader have more capacity, and therefore more success. So the growth mindset is really about empowering people to discover their gifts, strengths, and talents. And to create the most conducive setting to express that.

And just being able to really do this “job description” well is not aspirational enough. What you want to do is have some way of telling people that you want to see them grow in these four dimensions. Or how to be able to tell them how you see their potential evolving. If you can tell people where they're headed, they're more likely to get there.

A: You mentioned four dimensions, and I don't think that's an accident, because you do have a framework that has four dimensions in it, describing the different types of competencies that executives have. Could you walk us through what that framework is and also how you came up with it?

D: The first is awareness, and that's your ability to know what's going on around you, and in particular to know what impact you are having. Most people go through life surprised. If they were really aware of what's happening because of their actions and their expressions, they'd get less surprises. So, a highly competent executive is aware of how and what he's bringing is impacting the people around him, and that comes from self-awareness. You become aware of who you are and what's coming through you. And all growth starts with self-awareness. When you're aware of what's happening in you and where your strengths and weaknesses are, then you grow. That's why awareness is right up there as one of the four competencies.

Second is power, which is the power to get stuff done. It's also the power to confront challenges and the power to focus. It has to do with discipline and clarity.

It has to do with skillful handling of conflict. It has to do with being direct, upfront, transparent, and candid. An executive that doesn't have the power to get stuff done isn't going to get very far.

Third is confidence, which is a little more of an elusive quality. It's the ability to inspire others. But in many ways, it's among the most important things you want to see in a leader. You and I have both been in situations where we've hired a new leader for the same team, and suddenly, the team performs at an extraordinarily higher level. It's because of this quality of confidence, which is ultimately the confidence to be yourself, and therefore, to inspire others to be fully themselves and bring their best stuff. When the people around you are believing in a compelling positive future and wanting to bring their best stuff for you, great things start to happen. This doesn’t happen where the confidence is low.

And the fourth competence is connection. It's that ability to make people feel like they're part of the team, that they belong here, that this is a place where they're cared for, where it matters, that they are part of the community of the whole culture, and people feel like they've got access to you. They're not just foreigners in a strange land, but they're working with somebody who really gets that. When you have a team that feels like they belong, you get people willing to go the extra mile in ways that they just won't go if they're being treated like robots.

A: Absolutely. I remember when we first discussed this framework, there was a symbol of each of these four dimensions. Awareness was symbolized by the seer—someone who can intuit and perceive things. Power was symbolized by the warrior. Confidence was symbolized by the Queen or King because they have the gravitas that inspires other people. Connection was symbolized by an empath or the lover.

D: Those are Jungian archetypes, but the whole framework was originally developed by the University of Chicago. Both the psychology department and anthropology department got together. They studied how symbols, traditions, and rituals through the ages, connected indigenous people's imagery with Freudian, Adlerian, and then Jungian psychology. And a mentor of mine, Robert Moore, boiled it down to these four basic directions, and that's wonderful. And then it was translated into a very usable form by my very good friend, Cliff Barry of, who developed processes that help people grow in each of these four dimensions.

A: It's so powerful to think about these four. I don't think I've ever heard of an executive being evaluated based on these four attributes, frankly, outside the guide that we put together when I was looking to help the executives on my team grow in different ways. [Scroll to the bottom of this post to see that guide.] Why do you think that companies don't currently formally evaluate their executives on these dimensions or help train them on these things specifically?

D: Well, measuring self-realization growth as a human being and as a leader is a really hard thing to do. You could say it's subjective, and a lot of people have blind spots. They can't actually see how aware people are, or how powerful they are, or how connected they are, or how confident they are.

And other people see it in a strange way. It's like they want their people to just be more efficient or something. Or they want their people to be more nice. So, looking at four different directions gives you the chance to see through different viewpoints and have a more balanced view as a result.

A: It seems like very thoughtful CEOs who want to help their employees and leaders become fully self-realized would pay attention to this kind of framework more. Whereas if you're looking for someone who's just going to do what you tell them to do or mold into a particular narrowly defined culture, this is probably not a framework that you're going to be drawn to.

D: That's right. And the great leaders are people who encourage people to be fully themselves. So, if you wanted to do it with math or with a measurable academic framework, that's harder because people are complicated. And so you've got to be interested in them. Who are you? How can I help you grow? How can I help develop a competency that's really strong for you? How can I help you compensate for something that you're not well-developed in? And that curiosity, passion to know people and to help them be a full expression of their potential, that comes from inside the leader. It’s an innate desire to see people at their best.

A: When I started getting to know this framework with you a few years ago, I found it useful for personal development. These were four dimensions that really resonated with me in terms of helping me understand where I was strong as well as where I was getting my energy. And maybe also where I was over-utilizing a competency. Early in my career in particular, the warrior competency was one that I overused, and it burned me out a little bit.

D:  That's right. With the imbalance, too much focus on getting stuff done, not enough focus on the connection and support can be challenging for people. Then you can see what's happening for people just by listening to their stories and then see that in yourself.

One thing that's really important in working with people is that you are always looking for not what's wrong, but what's emerging. We want to see people and see where there's an opportunity to grow this capacity.

It's not really that you had a problem that you were too oriented in warrior. It's more that you had an opportunity to grow your capacity to connect and to grow. In particular, in your case, over the years, you've grown your confidence a lot. So, now you inspire people to go for something bigger just by your presence. People want more, they feel like they can give more of themselves, and that's made you such a more effective leader. But it's always growing a piece, it's not like correcting the personality.

A: You don't believe that every executive needs to demonstrate all four of these in equal quantities, right?

D: No. What I do think is that every executive should be in touch with how they are in each of these four dimensions. The skill of being a great leader is the skill of being authentic. So you're not going to try and be the ideal leader. Actually, that's a low confidence expression. I don't believe in who I am, I feel like I've got to try and be some model of what other people think I should be. And that's actually detrimental to leadership.

I really hesitate to tell people that there is an ideal here. There's a map in which you can understand yourself more fully, then leverage your strengths and find other people who are strong in the areas where you're weak. The most powerful thing a leader can do is just talk to other people. Find out where you're strong and leverage that. Then find out where you're weak and find other people who can help you with that.

A: So, if you are a CEO or founder recruiting your first head of sales, one of the things you should look for is the combined set of energies across these four categories that you and these head of sales candidates each represent. Because the person that might be the best head of sales for you is not necessarily the person that's the best head of sales for someone else.

D: Exactly. And you don't just want to say, "I'm no good at sales. I need a salesperson." You want to say, "I'm actually very good at getting people excited about a vision and I want a salesperson who's really good at grounding that and bringing that into an actual transaction."

A: That's so powerful. One of the things I often find working with executive teams is that, there's a lot of focus on who's covering which metrics to make sure all of us together are covering the full financial dashboard or operational dashboard. And there's definitely focus on if they all get along. But there's not often a lot of focus on the types of energies that they as a team need to demonstrate.

I mentioned this when I interviewed CEO Steve Sloan from Contentful a couple of months ago. Especially as you scale, there are a few key activities or behaviors that executive teams need to have, that are often not directly assigned to one particular function. So, sometimes they end up not getting done.

For example, cheerleading — being someone who's rallying employees, rallying your customers, rallying investors, getting everyone excited, being a kind of enthusiastic spokesperson for your company.

Some founders are that way, but some are not. And particularly, I tend to work with a lot of companies with technical products for their technical founders. Some of those are technical founders and they love being cheerleaders. Others don't have that energy. Or they're not drawn to that energy.

So your head of sales might not need to have that energy. But maybe it's your head of people, or maybe it's your head of marketing, or head of customers. Someone else has to exhibit that energy.

A related practical deficiency I found is that there needs to be someone at your company who can meet one-on-one with senior people at your customers, assuming you have some kind of top-down motion. You might be a PLG company primarily, but maybe you have bigger customer and there’s got to be someone at your company who can get on the phone with a senior person or customer and ask for forgiveness. Or ask them for their help.  Or build rapport with them in order to pave the way for the practitioner at their company to work closely with the more junior people at your company.

Going back to your framework, that might be the connection energy that someone needs to demonstrate. Or maybe it's the confidence one. But it's something that, again, doesn't necessarily belong in a particular functional job description. It's just that someone at your company needs to demonstrate it.

D: Yes. There are always things, whether it's external, with a major customer, or internal with either a troublesome or an important performing employee. The challenge for the leader is to pay attention. And you know that I suggest a Sunday practice and a Friday practice for leaders. On the Sunday practice, when you think about people, maybe there's four or five people that you write on a list. On the Sunday practice, just for 20 minutes, make notes about what's going on for them. What are their gifts, strengths, talents, and qualities? What are their challenges? How might you help them develop and grow? Is there an intervention or conversation you need to have?

It's about taking that meditative thinking time to pay attention to what's going on with the people in your world inside and outside the company.

And then the Friday practice is reviewing the week and seeing how well you did at the things that you thought could help this person or this situation. It’s about holding yourself accountable to the actions that you see a need for. Or the support that you want to give to people or get from people. And that's really important. It isn't just about running through week, after week, after week. Great leaders are the ones who stop, pay attention, and think about what's going on in what they see.

A: I want to talk about how your distribution across these four categories might change with how senior you are. I find I've changed over time. I don't know if that's a universal thing, but do you notice any kind of pattern in that way?

D: There are patterns sometimes, but mostly, I encourage leaders just for look off a blank slate. Don't necessarily expect somebody to become less oriented and power more oriented direction as they grow older. Men and women actually tend to grow in different ways according to some studies.

I encourage leaders to just look at what they see, and trust your own perception of how somebody is growing. Where somebody has a need, or where somebody could do with just being appreciated for their greatness. Be in the business of making other people feel confident about how great they are, feel how much they've got to give, and to be wanting to grow in areas where they can benefit from doing work or getting training. If you are just curious and passionate about that, you'll see it in people.

As you become more senior, it becomes more important to pay attention and have a growth mindset that you carry into your team. You’ll be wanting people to grow and talking to them about how they're developing, as human beings and as leaders, and making them feel like you really care about who they are and how they're emerging as people and what they're realizing in terms of their competence.

A: Applying that in the reality that we're in can be difficult. We’re often in a chaotic, very fast moving environment. Particularly, I mentioned seniority in my question because I often notice leaders expecting their junior employees to primarily exercise the power dimension in terms of being a warrior—getting stuff done, just get it done.

But as you know, every person is different, and a junior employee might be naturally gravitating more toward connection or confidence. And so sometimes with junior employees, they're almost like a shell of themselves at work because they're not given the permission to actually fully, even sometimes partially, realize themselves.

But at the same time, I've been in a position where I just need folks to get stuff done. And if you're a first line manager, you're held accountable to your ability to just get people to get stuff done. So how do you reconcile that tension?

D: First of all, I say again, if you can not just have your people get stuff done at the level they're currently at, but if you can grow their capacity to get more done, then more stuff is going to happen with less effort. People grow. So that's why we say people who are passionate about self-realization are more successful.

And it's no excuse that there's too much to do or that it's too chaotic. It's about practices. And some of the practices that you can do to grow just take a short moment. They don't actually interfere with your day. As with the example you talked about with senior people using junior people, one of the practices we have on our Numina team website is the feedback practice, which is something I recommend for leaders, especially if they want to grow awareness.

But you can have barometers in your team and people love to be asked to do that. I want you to watch me and see how I'm doing in connection, or watch me and see how I'm doing in power. Leaders can use the people in their team to help them become more aware of the impact that they're having. As a byproduct, that also grows the people in the team. It makes them feel closer and more involved, and makes the whole thing feel more like it's a human organism that's growing, not just a machine.

A: I want to come back to the set of expectations that you and I outlined a number of years ago. It's probably five or six years ago, when I was at Gainsight. I was in the moment trying to help the executives reporting to me grow as leaders. I didn't want them to just be functional leaders, which might be maybe what you need at a director level. I wanted them to do the things that a lot of CEOs and COOs want, which is to have them act more strategic. Have them inspire their teams. Not just get stuff done, but really empower their team members to do better things, longer term.

These are the words that we tend to use when we're trying to up-level an executive and ensure that we don't have to layer over them. This also applies to what we want when we hire an executive. We want to see them really grow as a leader.

I was noticing some deficiencies, like certain team members on particular teams might escalate to me about their manager. Or, for example, in updates, leaderswere giving a list of tactical things they were working on, but it wasn't necessarily tied back to the broader strategy.

I was thinking about, how I can communicate what it looks like to be an executive? Particularly, since as an executive at a $25M ARR company, we need different things from that person when our company gets to be $50M. But it's going to be the same person. You're effectively promoting them as you just keep them in the same role.

I was thinking about up-leveling and I told you that the four-part framework really resonated with me and asked how we can map expectations back to it?

Now, in retrospect, I'm wondering, was that the right approach? Because, to your point, we shouldn't necessarily be expecting every person to exhibit the same strengths in all four of these dimensions. On the other hand, it's a really useful framework for helping people fully realize themselves. So what do you think about using the four-part framework to set expectations for people?

D: It really does help people to give them a direction to go in. And it's more helpful to give them four directions to go in than just to say it's one direction, be a better leader somehow. This helps you expand in different ways. I recommend people choose the direction that they're strongest in to work on and also the direction that they're weakest in to work on.

So don’t necessarily work on all of them. But there's going to be good benefit you'll get from paying attention to where you think you are lowest. And then there’s a good benefit you'll get from asking how you can I leverage what your natural gift, talents, and strengths really are.

People already know how they want to grow. And so part of the skill of the leader is to get that out of the person. You can use language like king, warrior, magician, lover — or the corresponding dimensions of awareness, power, confidence or connection. But use something that helps people get an understanding of the range of that growth can happen in.

How do you see your potential? Who are you in your full potential? As a leader, if you know that about your junior people, and maybe you can map it onto something, but you've evoked in them a desire to fulfill that potential just by having them express it in their own language.

A: That brings me back to something you said earlier in the conversation. Developing your abilities as an executive starts with self-awareness, with awareness being the first competency. And it's a delight to coach someone who is self-aware. It's very hard to coach someone who's not self-aware. And it makes me wonder if we should be hiring executives first and foremost based on their self-awareness. In common startup culture, this is not something that we necessarily explicitly talk about all that much. And actually, if anything, in certain roles, you might think you want someone who's just a gunner, which may not be maybe counter to the goal of finding someone who's self-aware. What do you think?

D: Well, if you’re talking about a culture fit, you look at all four. I don't think you just hire for self-awareness. You want to hire people who are effective, therefore powerful. You want to hire people who believe and are capable of creating a buoyant atmosphere around them, who add to the sense of belief in the team as a whole. You want people who are fun, who are connected, who are in touch with their own feelings.

So, you are looking at it all, and then if you're putting together a team, you're looking at a balance of all people. You may suddenly realize you've got a lot of people who are just in their heads the whole time. They’re focusing and have very high awareness, but they’re not very good at actually connecting. Then maybe you need to put some people in there that are good at connecting or do some things together that help with the connection.

It's very much about an evolving picture rather than a form that you just impose and it's going to work on all situations.

A: Absolutely. In that framework that we put together about expectations for executive competencies, within each of those four categories, we had put a time dimension. So for awareness, for example, there's going to be a way that you need to be aware of the past, aware of the present, aware of the future. For the power competency, you need to be powerful with respect to the past, the present, future. And we talked about more specifically what that means. But I wonder for you, why do you think it was important to include that time dimension?

D: And we evolved that together. I remember when we were working on it, and we were noticing that you might have people who were competent in one way, but they weren't very skillful with understanding how we got here. And the past dimension can be either how we got here in terms of the tasks evolving or the people evolving. But sometimes, using a model like that can just help people notice that they get stuck.

They think that good performance is going to be within this narrow dimension. They’ve got to be effective in the present, and the future doesn't matter. I like to lift people so that they can see a bigger context. Maybe they’re really good at understanding how we got here, but they’re not very good at inspiring people about where we go. And then that tells you that want to develop that or find people who can help you so that the whole team is more balanced in that way.

So I encourage people to use whatever language works for them. But this certainly helps. Ask how can you apply this in the past dimension? How can you apply it in the present dimension? How can you apply it in the future dimension. It helps people see where and how they need to grow, and helps people free up self-defeating concepts that may be limiting them.

A: I love that idea of lifting people up. That resonates in a lot of ways. David, we're almost out of time here, so I'd love to know what's one final tip or suggestion you would have for CEOs and founders?

D: First of all, be passionate about growing the capacity of your people. And that really means helping them be more fully themselves.

And I want to leave people with the power of simple practices. Carve out 20 minutes for yourself every Sunday with a piece of paper, where you make notes about your people. What are their strengths? What are their weaknesses? How can I help? How is this person challenged? What do they need from me? It's the act of paying attention, which will help you as a leader or an executive to become a really competent coach who helps grow the self-realization of the people they work with.

A: I love that so much. This is so fun, David. Thank you for joining us, and I hope we can do this again someday.

D: Me too.

Preface: Guide to Executive Competencies

I’ve included below the guide that David and I created to help coach my executives. This framework assumes the following:

  1. Being a great executive is not the same as being a great functional leader. There’s also plenty of content on the expectations for functional leaders, e.g. what competencies a sales leader should demonstrate. But not much has been written about executive competencies, which is the focus of this framework.

  1. Executives need to traverse the full range of time. They need to derive the right lessons from the past, execute with urgency in the present, and pave the way for success in the future. So this framework covers all three periods - past, present, future.

  1. There are 4 types of competencies. Each one has a symbolic figure. The Seer represents the competency of Awareness: how can we see the world accurately? The Warrior represents Power: how can we shape the world? The Queen/King represents Confidence: how can we inspire others? And the Lover represents Connection: how can we create bridges to others?

This framework can come in handy when you’re setting expectations for new hires or recently promoted executives; when you’re evaluating performance; and when you’re helping a functional leader chart their career path.

Feel free to share this with your team!  


Dimensions of Executive Competence

#1: Awareness (Seer)

  • Past: Explain historical trends through rigorous learning by leveraging data, anecdotes, industry benchmarks, intuition, personal experience and exposure to others’ experience

  • Present: Allocate capital (time, budget, and mental focus) to drive leading indicators and then lagging results

  • Future: Craft a compelling roadmap for 3 months, 6 months, and 12 months that is aligned with company strategy

#2: Power (Warrior)

  • Past: Take 100% responsibility for your team’s results and get support where there are gaps

  • Present: Challenge your team, your peers, and yourself to bring high-energy, consistent, persistent execution

  • Future: Create clear commitment to near-term and long-term goals that are both a stretch and attainable, based on well-informed forecasts

#3: Confidence (Queen/King)

  • Past: Make sure your team, other functions, and boss, feel seen and appreciated for the contributions they are bringing

  • Present: Articulate and model the values and actions that you expect to see in your team

  • Future: Inspire others to give and to grow by painting a compelling, purposeful vision of the future

#4: Connection (Empath)

  • Past: Understand others’ motivations and express empathy for their personal challenges and sensitivities

  • Present: Foster an environment of diversity, inclusion, belonging, teamwork, growth mindset, and bottom-up innovation

  • Future: Lay out pathways for each individual’s development, via planning of organizational structure, key roles, and career paths, and by attracting and retaining worthy mentors

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