Confidence and Collaboration with Coach Chris Leonard

For this blog post, I was fortunate enough to have one of my good friends, Chris Leonard, join us. For a smoother read, this blog will be composed in script style. Enjoy Chris’ wealth of knowledge and experience.

About Chris

Lauren: Chris is a fellow coach that I have worked with at a couple of different companies. He is here to help you, as new leaders, kind of figure out what’s going on for you. So, Chris, why don’t you start by telling us a little bit about yourself?

Chris: So I had an interesting path into coaching. I started out in the music industry of all places as an audio engineer and spent a lot of time, both in studios and riding on buses, with the people I was working with, which is an interesting way to learn the art of collaboration and the art of leadership. It was also a great exercise in learning how to ship products every day. The show went on every day, regardless of whether you felt like you were ready or not.

I often use the old adage that’s attributed to Lorne Michaels: SNL doesn’t start because the show is ready. SNL starts because it’s 10:30. So I had to really embody that for a lot of years. After that, I took a hard left turn during the recession into the world of technology and pretty quickly rose as a project manager and then into scrum master and coaching, which was a great way to learn how to orchestrate collaboration and help leaders in a totally different context. I have a little bit of one-on-one coaching in the small business world too, which I’m really enjoying.

Lauren: You have a really widespread breadth of experience coaching different industries, it sounds like.

Chris: I would like to think so.

Lauren: I don’t talk about this a lot on my channel, but I actually started in the entertainment industry as a lighting technician. So we have a lot of similar backgrounds. Segueing into actually talking about our new leaders It sounds like you have a lot of different experiences in different industries. So you’ve seen a lot of different styles of leadership. In your opinion, what are some of the key attributes that make a leader successful, regardless of what kind of style of leadership they actually use?

Chris: The best leaders I’ve seen have a combination of things that I think are really important. I think empathy for the people on the team is really important because it goes into helping them get things out of their way. A lot of it comes down to being able to put your perspective aside for a few minutes and really see the world through their eyes.

Because you won’t be able to understand what they’re going through and what’s in front of them if you’re too distracted by your own perspective and agenda during the conversation. You’re just going to see a person not doing what you want. And it changes the relationship from an adversarial one to a very cooperative one when you make that transition. So openness and curiosity go with that too. I think those are important as well.

You kind of need to be the watchtower for your team, taking in new information and new perspectives as well as looking out for dangers that they can’t be totally on the lookout for because they’re down in the weeds, getting the work done.

And then, I think, the third is the confidence to stand by your convictions and your decisions. When you do make a decision, right or wrong, that’s the direction you’re going, and you’re going to stand by it because if a leader doesn’t do that, if it becomes obvious that every decision is negotiable and every decision can be manipulated with someone screaming loud enough or making the right argument after the fact, it creates a lack of confidence in the entire environment. People don’t really know if any decision is real because it could change tomorrow or become all political.

You’ve got to create enough confidence in the environment and the decisions that are being made so that people can assume a matter is settled once the decision is taken.

Lauren: Yeah, you know, I totally agree with all of that. Let’s talk a little bit more about confidence. I talk a lot about confidence in my blog posts and my videos. What do you think a leader can do, especially a new leader, to help improve their confidence? Because a lot of new leaders step into their roles, they’re not really sure if they have the knowledge to make these decisions or if they really have the authority to make them. What do you think a leader, especially a new leader, can do to help become more confident in their role in their decisions?

Chris: You know, I think about this sometimes from the perspective of being a parent. Sometimes, as a parent, I think, who recruited me to this thing? Who decided I was qualified to do this? But I am here and you couldn’t replace me with somebody else and have them easily do as good of a job as I am, because I am the only me that my child has.

Consequently, you’re where you are in your organization for some reason. And the totality of who you are is all part of that reason. You couldn’t easily replace somebody else with you and have the same result. You’ve got to bring your totality of who you are to the job because it’s part of what got you here. It’s about why you were chosen or why you found yourself there. People look up to it and appreciate it. I think that’s the first thing. Understand that you are not an easily replaceable person. It’s not like you can just switch yourself out with another leader and get the same results.

I think the second is being curious and open and realizing you don’t have to have all the answers is really important to gaining confidence as a leader. Because if you take upon yourself the weight of every decision and the way of having to be right all the time, this burden of having to always be right, never admit you’re wrong, or never admit you don’t know is a thing a lot of leaders take upon themselves unnecessarily that I think makes the job a lot tougher.

The best leaders are good at orchestrating the best answers out of their team when nobody really knows, but you can orchestrate some kind of resolution to the question that everyone can commit to, even if they don’t all totally agree. Those leaders tend to get the team to pull in that direction really consistently and thoroughly, and at least find out if they were right or not.

So, I think, it really gives you a lot of confidence when you make that admission that you don’t know the answers; you don’t have to have all the answers, but that you’re the right person to help the team find it together.

Lauren: Yeah, I think new leaders put a lot of pressure on themselves to have all the answers when, just like you said, they don’t have to have all the answers. That’s not the point of being a leader. The point of being a leader is to help everyone else figure out the answers with you and move in the same direction.

Chris: Look at a lot of the best leaders, or at least like the leaders who’ve come such a long way and are most known for it. I mean, I think about leaders who’ve been around a long time, like Bill Gates or somebody like that.

They’re lifelong learners. There’s a reason that everybody will click on Bill Gates’s or Barack Obama’s reading list; it’s because these people are constantly vacuuming in information, and they’re very curious. That level of curiosity may look like it makes them sage and know it all, but actually it’s the opposite. It’s an admission that they don’t know everything and that even for as far as they’ve come. They know there’s a lot more they need to know to face the future and to be a leader in that context. They will get to understand it soon. Taking in lots of information and being a lifelong learner—that’s one of the skills you really have to model as a leader. And it gives you confidence if you’re constantly learning.

Lauren: Yeah, that curiosity to understand, like, hey, I know I don’t know everything, so let me go learn more. That applies not only to reading but also to talking to your teammates, talking to your coworkers, you know, talking to other leaders—it really kind of snowballs into this, you know, collaborative curiosity.

Chris: Yeah, absolutely.

Lauren: What a lot of new leaders struggle with is, you know, that transition from teammate to leader and knowing that, okay, now I have to hold these people accountable. Whereas before, I was just a fellow teammate, and we were, you know, pulling along together.

How can these new leaders take on this new role of now being responsible for these people as opposed to just being their friend or their fellow teammate? You know, how does confidence play a role in helping them navigate this new world that they’re in?

Chris: Yeah, I think my wife went through a situation recently where a good friend on her team became the boss and their relationship has changed. But, I think it’s a positive example because the rapport that they had and the trust she had in that person before this change is a big part of why that person has been successful because she has built up all this goodwill as a peer of the team and they really trust that they’re in good hands now.

When you look at that situation, don’t see just the risk of the good relationships that you have with your former teammates. See that as an asset. You have their goodwill. They want you to succeed. They’re probably glad you’re there, as opposed to some outsider who they can’t trust and don’t know; use that to your benefit. Use that to give you confidence that, again, they want you to succeed and that you’re all in this together. You leading them is not something you’re doing to them. It’s something that they have very much been part of and that they will continue to support until they don’t. Right? But you would know it if they didn’t.

If they’re still your friends and they still want you to succeed, and you guys still have great conversations together, then they do. Continue to be you, because you are who you are. Having the interest that you have, the sense of humor that you have, and relating to them the way that you do is part of why you’re here again, and if you let all that go away to kind of put on a mask of professionalism over who you are, then you probably will start to erode that goodwill. But by continuing to embrace the relationships you have, even as you just have to make the decisions that you make, they’re going to respect you for them. They’re going to continue to be glad that, again, it’s you and not somebody from the outside who they don’t know and don’t trust and whose intentions they don’t understand, so continue to be you.

Lauren: That’s great advice. When you have to start holding them accountable, you already have that relationship—that rapport with people. So it’s a little bit easier to go to them and say, Hey, it looks like this; you know, metric isn’t what it is or where it needs to be. What can we do together to kind of help, move things along, change things, or whatever? You have that history with them. So it’s a lot easier to go back and have those conversations. People assume it’s going to be harder because you have a history, but it actually ends up being easier.

Chris: And they know you’ve done the work before, too. That builds confidence that you’re making the decision from a good basis of information and empathy with them, as opposed to somebody coming in with a more academic perspective who doesn’t really understand them.

Final Thoughts

Lauren: Yeah, for sure. What final piece of advice would you give to a new leader just starting in a new role? What would you do to encourage them to be successful?

Chris: I think a big thing is to have realistic goals for yourself and realistic goals for your team. The two biggest mistakes you can make are to not have any goals at all for yourself or your team, or to be so wildly ambitious for you and them that it becomes demotivating and disengaging.

I’ve had so many leaders fall over either of those guardrails and so few managed to stay on that road of giving you a useful goal that we can all rally around and giving you a personal goal that is both useful to your context and helps you move forward in your career. So having that for yourself, uh, and for your whole team is really important.

Whether that means taking a walk to come up with that stuff, spending a day off thinking about that stuff, or spending some time reading up on it, asking peers, asking your leader what the right goals should look like, and reading about what good goal-setting looks like, that’s really important.

I think that’s the single biggest thing I would give to new leaders: don’t just see goal-setting as a formality. It is really integral to how you lead and how you build those relationships with your team.

Lauren: Yeah, for sure. If people want to get in touch with you, how can they do that, Chris?

Chris: I’m on LinkedIn: linkedin.com/in/LetsHireChrisLeonard or csLeonard@gmail.com.

For the sake of readability, some minor adjustments have been made to the interview transcript. Instances of stumbling, superfluous words, and repetitive phrases have been omitted to enhance the flow of the conversation. These edits were made with the intention of presenting the interviewee’s thoughts in a clear and concise manner without altering the substance of the discussion.