Solving the Right Problems with Wayne McCulloch

In this episode of the B2B Leadership podcast, best-selling author and leadership coach Nils Vinje sits down with Wayne McCulloch, Chief Customer Officer at WalkMe. (note: at the time of this recording, Wayne was working for Google)
Wayne and Nils cover a lot of ground from how Wayne earned his first leadership promotion to the top 4 leadership characteristics that he looks for in any leader.

In this episode...

1:48 - Wayne's two careers - Software training and Customer Success...
3:50 - Solving a problem no one asked Wayne to solve - How Wayne got into his first leadership position...
8:10 - The role of psychological safety in leadership - Give people permission to solve problems...
12:13 - How Wayne found out he was leading the wrong way - A very important conversation with his CEO...
15:30 - How to practice vulnerability - Acknowledge you don't have the answers...
18:40 - Getting promoted during an interview process - Asking powerful questions...
23:45 - You are a mountain climber, explorer, or deep diver - you need to understand how all the pieces fit together...
28:48 - Vertical versus horizontal focus - The more senior you are in an org, the more important the horizontal focus...
29:40 - Wayne's top 4 leadership characteristics - Coaching, Accountability, Empathy, Gratitude...
39:05 - Wayne's advice if he could go back in time - You are not as good as you think you are but you are not as bad as you think you are, and become known as a problem solver...

Connect with Wayne McCulloch at

Learn more about your own leadership style at


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Wayne McCulloch is the Chief Customer Officer at WalkMe. We had the privilege of talking with him about his experiences and leadership advice.

As a C-level executive, Wayne has a lot of responsibility inside of a very large organization. However, it wasn't always this way. Continue reading to find out more about Wayne's leadership journey.

Wayne's two careers - Software training and Customer Success

Wayne McCulloch started his career in B2B Software around training enablement, adoption, and education. He then transitioned his career to customer success, professional services, support, and all the components of the post-sale organization.

Solving a problem no one asked Wayne to solve

How did Wayne go from an individual contributor level into a leadership position?

Even without proper leadership training, Wayne was able to transition from an individual contributor to a leader by being brave enough to say that there's a different and better way to run their organization, which then resonated with people.

Wayne said he first recognized that the way their organization was running had not evolved in decades and so he decided to come up with a different way to run the organization. He then presented the idea to the CEO of the company.

No one asked him to do that. He said being an Australian makes him proactive and that even if no one is asking, he would still give out his opinion on solving the problem once he sees one.

Taking a look at the situation, assessing it on his own, coming up with an idea, and then presenting the idea on how to do something different enabled Wayne to be seen as a leader.

It is important to be brave and grab the opportunity to be the first in presenting the solution to the problem.

The role of psychological safety in leadership

If you're not naturally proactive in sharing your ideas, here's another way of doing this.

Have you heard of psychological safety?

Psychological safety is about creating an environment for people to feel safe in expressing their feelings and thoughts.

Wayne wanted to formalize this and created a program that would give his people a voice and permission to put time and effort in identifying problems and finding solutions to them.

This in turn gives his people a sense of accomplishment that they've helped the organization address the challenges they see.

All the problems that we face don't always require silver bullets.

Little improvements make a difference. Wayne said the impact doesn't have to be big, as long as we're getting better.

Wayne recalled one of his leadership downfalls in his first year. He thought he should have all the answers to every problem. He forgot he was empowered as someone who actually lives the problem to solve the problem.

He realized later that being a leader doesn't mean you have all the answers to all of the problems. A leader just needs to lead the team and not to solve every problem.

How Wayne found out he was leading the wrong way

Wayne had a one-on-one coaching session with his mentor, the CEO of the company.

His CEO told him that there's a problem with the way he leads his team. His mentor said that Wayne has been giving solutions to problems he hasn't actually experienced.

His mentor explained that being a leader doesn't mean you should answer all of the problems on your own but to allow your people instead to participate in solving the problems. To allow your people's ideas to surface and create successes for themselves, for the organization, and their customers.

Wayne said that was a very important and pivotal conversation in his career. And from that point on, he started to do things differently in leading his team.

"None of us is as smart as all of us." This is one of Wayne's favorite quotes.

Being a leader is helping other people discover the answers. Your people will follow you as the leader because they know that you can help them get to another place they might not have been able to get to on their own.

How to practice vulnerability

The sentiment that everybody else on the team has the answers to all of the problems and not just the leader made Wayne very vulnerable.

As a leader, Wayne cannot say "Hey, everyone, I don't know what's going on, I have no idea what to do."

But as a leader, Wayne said he has to be genuinely honest, open, and comfortable with his team. Getting them involved by allowing them to have a voice while trying to identify a problem or come up with a solution is tough, but as a team, as long as they could come to some conclusion, it's powerful.

It is important to have that unified vision in the team. Even an ordinary idea with everyone's energy behind it can be great. It doesn't have to be the best idea as long as everyone is actually executing against it.

Wayne believes that you have to go slow to go fast which means you have to take a step back and involve a few more people, and you get some more insight that can make the difference between a good idea and a great idea.

Getting promoted during an interview process

Wayne had been on a journey of increased responsibility throughout his entire career. Sometimes this came with a promotion and sometimes it was just extra work for no change in pay or title. Nevertheless, continuing to grow and to learn has been pivotal for Wayne.

One promotion he had gone through that he considered important was when he got promoted during the interview process. Because of his broad knowledge, he was able to identify problems in the interview and articulate how it is not a department problem but a philosophical problem with the company and many people and departments would be needed to solve it.

Identifying the problem, articulating it and presenting an approach on how to solve it was massively impactful for the company.

Being bold in bringing ideas to the table brought Wayne to where he is today.

Wayne said that the ability to explain something that's unknown will elevate your credibility tremendously. And it only comes because you think about something more broadly.

Being able to understand how the pieces fit together gave him the ability to explain problems that other people didn't get, which means he could do more.

You are a mountain climber, explorer, or deep diver

You are a mountain climber, explorer, or a deep diver in your career. You either want to be the CEO, you want to try all different roles, or you want to be the best that you can be at just that role and be there forever because you love it.

For Wayne, being an explorer is an important part of your career journey and understanding how other functions work. If you want to be a mountain climber, you've got to understand how all the pieces fit together. You have to learn empathy by spending time with people even if you're not working with them, to know and understand how difficult their job is.

During the interview, if you ask the right questions, highlight the holes, and then come up with a solution for how you would solve the problems, it will change the dynamic of the interview completely.

Being able to demonstrate a much broader set of capabilities you can bring to the company, either to be used now or later as the company wishes, creates a versatility in a leader that separates you from other leaders who have more experience than you.

Wayne has been using the same formula during his interviews and that is demonstrating an understanding of the mechanics and knowledge of running the business that's way bigger than what the company is looking for.

Vertical versus horizontal focus

Wayne believes that the more senior you are in an organization, your focus needs to switch from vertical to horizontal. During the interview process, what's expected from him was to bring value that has a horizontal impact not just vertical.

Wayne's top 4 leadership characteristics

What are some of the traits and characteristics from other leaders that have influenced Wayne in his own leadership style?

Number one is coaching. Wayne's most important job as a leader is coaching. This characteristic stood out the most for him. He doesn't tell his people the answers to the problem, he teaches them to discover the answers on their own.

Number two is accountability. Wayne said coaching and accountability work side by side because you can't hold people accountable if you're not coaching them the right way and giving them the right tools. Not all leaders have accountability because they don't do coaching the right way.

Number three is empathy. Being able to demonstrate empathy is all about understanding that everyone is different and that everyone needs something different when they're going through difficult times in their lives. The leader's job is not to offer the solution, their job is to ask the person what the solution is for his or her own problem.

Number four is gratitude. A leader must have gratitude for his or her people, be appreciative of their vision and execution, and for having success. Because not all the best ideas and execution of ideas will come from the leaders, they will come from the people.

Coaching, accountability, empathy, and gratitude are the four incredible elements of leadership for Wayne and coaching is the foundational piece.

Wayne suggests that new leaders should take note of these leadership characteristics so that when the time comes that they have to interview their next leader, they can see if this leader will help them become a better leader.

It's important you are aligned with the leader you are working with and that can be of help in bringing out the best in you.

Wayne's advice if he could go back in time

If Wayne could go back in time to when he was still new as a leader and give himself advice with everything he knows now, the first thing he would tell himself is you are not as good as you think you are but you're not as bad as you think you are either.

Having that balance is important because some people believe they're better than they are and some people have imposter syndrome and struggle with that.

Wayne said that you have to always challenge yourself to be better. It's not about being the best leader or having the best ideas. It's about how you can make yourself better.

The second thing is to not focus on the things you care about, but instead focus on the things that others care about that are really important to them because this is how you demonstrate value to the company and others. When you do this, they will welcome you in to give you the opportunity to go work on the things you want to go work on.

In leadership, there will always be problems, that's guaranteed. But the better your team is at solving these problems, the better off you'll be.

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