Michael Watkins: Embracing Self-Doubt & Thriving During Transitional Periods

Michael Watkins is an established author and seasoned advisor for C-level executives that are eager to thrive and take on new, more challenging roles. Michael helps leaders navigate turbulent times by providing them with the tools and resources they need to take new roles, build out their teams, and transform their organizations.

Passionate about leadership and optimizing transition periods, Michael is known globally for helping senior leaders achieve peak performance through his proven 90 Day Acceleration methodology. Listen to this episode (or read the transcript below) to learn how you can improve and perfect your craft as a leader.

1 How did you become so interested in transitions?

I realized that I moved almost every year between the ages of 3 and 10 because my dad worked for Ontario Hydro, and he was building dams and power lines in the north. I probably went to over 8 different public schools, so I became really good at fitting in and adapting. I got really good at going to new places and establishing myself, but it wasn’t until years later that I realized that it was something that I intuitively learned to do. The notion of transition is something that I’m very interested in, even after years of studying.

2 How has your advice for leaders changed over the last 20 or 30 years?

I continue to learn and every time I learn something new, I incorporate these ideas into the framework. I also have a consultancy company that works with leaders so that helps me stay informed and refreshes my knowledge.

In terms of larger trends, technology, virtual work, and transitioning successfully to remote work is something I’ve been extremely interested in, even before the COVID-19 pandemic. I actually just co-authored an article in the Harvard Business Review about onboarding new leaders remotely and it speaks to how the process has completely evolved and how different it is in terms of how you can build connections. Transitions have also become much more frequent, so we dive into current happenings as people continue to move through roles at a more rapid pace. With COVID-19, everybody is in a constant transition, so I think there’s a lot that’s currently changing.

3 What is the main difference between onboarding a leader remotely versus traditionally?

In some ways, I think it’s easier because you can connect with almost anybody and it makes the playing field more even but it can also make it harder because it may not be organic, and you may not have the resources and contacts you need.

If you’re going to successfully onboard an employee remotely, I always recommend that an organization be structured, and more organized than they would normally be. It’s important to be intentional about who you’re connecting with and the information you’re sharing.  As a leader, I think it’s extremely important to be specific about what you need so you can make sure you’re getting what you need to be successful in your role.

4 Why do you believe you have to watch out for your strengths?

Something that I like to do as a thinker is to identify things that people believe are true but may not necessarily be true. There’s lots of conventional wisdom around identifying your strengths and leveraging them to be successful as opposed to the way we used to talk about it, which was to figure out what your development needs were and to try to close those gaps. The reality of the situation is that you need to do both, and you need to find a balance of honing in on your strengths but also closing the gaps or improving some of your weaknesses.

For me, it’s all about being very clear-headed about what you need to do well and be successful in your role. If you’re not clear about the destination and you only rely on what you’re good at you’ll get stuck in a comfort zone trap. What got you here may not necessarily be what gets you to your next destination. It’s important to be aware of conventional wisdom and understand why it’s there.

5 When might it not be wise to have a broader vision for a company?

Personally, you should have a solid vision of where you’re going but it’s also all about timing. Creating a shared vision should be part of a larger conversation where key stakeholders determine if it will be valuable. What you do is put in place goals and objectives. You get some plans in place, you do this all in analytics, you cut some things. You reshape the team. And then maybe at some point, you start taking that team, once you’ve got them aligned and built down the road of “Do we need a shared vision?” And by the way, that should be a conversation. Do we need it? Is it valuable? The purpose of a vision should be to inspire people and if you can’t inspire people, you shouldn’t be trying to create a vision.

6 What percentage of people go through self-doubt while transitioning?

90%. I think initially when you take a new role you’re extremely excited but then sometimes the self-doubt starts to kick in and you may feel like you’re not fully ready for the transition. There are models of transition that are really about the emotional cycles that you tend to go through like excitement and frustration and I see almost every leader I work with go through it. I’m currently working with a senior leader from a pharmaceutical company based in Switzerland. The organization is mostly based in the US and he hasn’t been able to move because of COVID so he’s gone through a lot of frustration because he can’t engage the way he normally would.

Having people that can help you stay within some sense of equilibrium when you may be going through something difficult is really important. Finding people that can help you sustain your energy during tough times makes all the difference.

7 Do you think self-doubt tends to set in more with long-term projects?

One of the models I built for The First 90 Days is called the STARS model and it stands for startup, turnaround, accelerated growth, realignment, and sustaining success. It focuses on different types of situations you may inherit and how you operate differently depending on which one you’re in. 

Of those five, I think turnaround is the easiest because you can go in and do some diagnostics. You know what to cut and who to move and it’s often pretty clear, especially at the beginning. If your goal is to accelerate growth, to sustain success, or to change a business it can get really hard and your frustration levels may start to rise so yes, I do believe that self-doubt tends to set in more with long-term projects.

I think it’s healthy to have some anxiety that keeps you on your toes. It helps you improve, and it helps you learn. The day you stop thinking you need to adapt or learn you lose a lot.

8 Can you define and expand on the action imperative?

The action impactive is basically the inner pressure you feel to do something or take action. It’s the trade-off between doing, being, and feeling anxiety around taking some form of action. It’s all about finding the right balance between learning and connecting, making decisions, taking action, and deciding when to begin to shift between the two and not doing it before you have a reasonable foundation.

9 Is it the leader or the teammate’s responsibility to adapt?

For me, it’s more about biasing yourself in the direction that it’s your responsibility to make the relationship work and if they meet you part way, fantastic, but don’t assume that’s going to happen. It’s more about your mindset and having the perception that as the new person, it’s your responsibility to make the relationship work.

If you find yourself working for a servant leader that wants to connect with you and make sure you’re engaging it’s great, but you shouldn’t count on it happening. For every servant leader, there’s someone who isn’t a servant leader, and they may even be an anti-servant leader. It’s all about biasing yourself and going in with the proper mindset.

10 Is it challenging to get honest feedback as a leader?

I would say that it’s generally difficult for leaders to get feedback and the higher you go the more difficult it gets because you don’t always have people to talk to. It can be lonely at the top. As a CEO, you’re lucky if you have a few close advisors, you may not have any peers and you also have to be very careful and very direct with the people you report to or report on.

People also have a tendency to not want to give new peers feedback. They want to give them time to find their feet and foster a positive environment, so people generally tend to be pretty hands-off so part of what I teach in coaching is to go in and get the feedback. I have an instrument that can be used to go in and get the feedback and I build that into what I do. The way I add tremendous value as a coach is to make sure that you as a leader don’t go too far off course.

It’s all about genuinely trying to get feedback. You can even set up an anonymous survey with three or four questions related to your performance and prompt your peers to fill it out. It doesn’t have to be complicated and you can basically just make use of the technology you already have at your disposal.

11 How do you feel about forming friendships throughout the organization?

I think it’s important to be friendly and to have friendly relationships and connections but whether you’re actually making friends is a different question because you’re generally going to have to make really hard calls about these people and their performance.

In my book Master Your Next Move, I wrote a chapter about leading former peers and there’s one example where someone had a reasonably close relationship with one of her peers and was competing with one of her other peers and she then got promoted and ended up having problems within both of those relationships. The competitor was annoyed that they didn’t get the job because they were really good at what they did and all of a sudden, the person that was promoted was having to conduct performance reviews on her friend and it starts to become really hard to separate the relationship.

Whether you have friendships or not you at least have to be perceived to be accessible, because that’s indispensable for any leader.

12 Do you have any tips, resources, or words of wisdom for leaders that are looking to improve their craft?

Before I was a leadership person, I was a negotiation person and an influence person, and I think there are tons of resources out there in negotiation, influence, and meditation that prove to be beneficial for leaders and these are skill sets that every leader should dive into. A great book to reference for these kinds of things is Crucial Conversations and there’s also a book called Meditation for Managers that’s really good. There’s also a book called The Art of Negotiation, and it does a really good job of focusing on influencing, negotiation, and conflict management.