How to Manage Leadership Stress Using C.B.T.?

For the last couple of years, I’ve been in leadership positions at a bunch of companies. In my work, marketing is high stakes. Marketing is directly responsible for new business (due to a product-led business model). It can get stressful.

For the last year or so, I’ve hired a mental health coach to manage my stress at work. One of my biggest learnings in a leadership role is that your mindset is everything. To be a great leader, you need the right mindset.

Now I’m not going to tell you today how to think like a leader. Plenty of people have already written about that. I’m going to talk about reframing your current thoughts and improving your mindset as a leader. This is based on my own experiences.

I’ll talk about three cognitive distortions commonly found among leaders.

Black or white thinking

We’re accustomed to believing that everything in life or work is either black or white. While the fact is 99% of people live in the grey area in between. Let’s see that with a couple of examples:

  1. I’m either a head of marketing (black) or I am not (white).
  2. Are we a successful startup (black) or are we not (not)? What is the universal definition of success really? None! 80% startups live in the grey area where they’re making some money and building a business. A lot of them are happy about that. I think that’s a successful business too.
  3. Am I a good manager or bad?
  4. My CEO thinks I’m shit or really good at what I do. Most executives lie in the middle of that.
  5. I either suck at working out or I’m great at working out. The grey area here might be that I be working out 1-2 a week but I’d want to work out 4-5 times a week. Does that mean I either suck or I’m great? No!

The majority of companies, executives live in that grey area. I’d even say that everybody lives in a grey area, there is no true black or white. That’s important to remember when you’re in a leadership position because you don’t label yourself as a failure or success. You’re in the grey area, the messy middle, which is where most people live, which isn’t talked about much. That’s perfectly okay and you should be happy to be in the grey area too.

Comparison: You win or you lose, there is no middle ground

Have you ever compared yourself with others? Of course, you have. Some examples:

  1. “Person A is so successful as a team leader at such a young age. Look at me, I’m doing the work of an intern. He’s a successful VP, I’m not even a VP. He’s a winner, I’m a loser. I’m not interested in this rat race anymore.”
  2. “Person A plays such amazing drums and he learnt it in 5 years. I’ve been practicing playing the drums for 10 years and I’m not half as good. He won, I lost. Why care about playing drums again?”
  3. “Person A has such an ideal partner, while I can’t even find a partner. He’s got his life sorted, while I’m in a mess. He’s a winner, I’m a loser. Why care?”
  4. “Person A makes so much more money than me, while I’m hardly able to handle my own expenses. He’s so successful in his career, while I flopped. He’s a winner, I’m a loser. Life is so unfair.”

There’s a major issue with this thinking. When you compare yourself to others, you never have full information about the circumstances of the other person.

Perhaps person A spent working 100 hour days for many years, sacrificing weekends, going to therapy to get that VP of marketing position. Maybe person A comes from a family of musicians and has been learning percussion instruments from age 5. Maybe a person’s husband might look perfect on paper, but his personality might be completely different from what you want out of your partner.

You never know have full information of the circumstances when comparing yourself to others. BUT you do have full information of the circumstances when comparing yourself to your previous self. That’s the only helpful comparison. You have full information of what got you to where you are.

The next time you catch yourself comparing with others, remind yourself that the only helpful comparison for self-improvement is you vs what you were.

I’ve made this mistake so-many-times all my life and it was a transformational mindset improvement for me. That’s because now I don’t worry too much about why the other VP of marketing is so successful. Instead I try to unpack that other person’s success factors and apply to them to my own journey and the only helpful outcome is how I perform vs my previous performance.

Worst case scenario vs best case scenario thinking

I’ll admit to a horrible secret about myself. I prepare myself for the worst-case scenario is EVERYTHING. While it can be helpful sometimes, when you think about the worst-case scenario about everything, it affects your mental health. That’s because the world comes across as dark and depressing, instead of a world full of possibilities and miracles.

Some examples of worst-case scenario thinking:

  1. if I don’t do this project well, I’ll get fired
  2. if I keep my bag in my hotel room when I’m out, my bag WILL get stolen

Pause for a second. Let go of all the negativity for a few seconds while I ask you this question:

What if everything you wanted went as planned? What if you go what you wanted? What would that look like? How would you feel?

– The Miracle Question

Is the objective to avoid the stress or manage the stress?

Does stress ever go away in our jobs? I’ve got good and bad news for you.

Bad news: No. Stress is always going to be there.

Good news: You can always manage the stress and it starts with acknowledging you’re stressed and finding the source.

How can you manage the stress?

  1. Speak with a therapist and document your journey (highly recommend).
  2. Understand Cognitive Behaviourial Therapy (CBT).
  3. Try out the questions and exercises in Feeling Good by David Burns.
  4. Chat with a mental health coach chatbot like Woebot.
  5. Write your thoughts out. Have a dialogue with yourself (for advanced practitioners only).

Once you understand where the stress is coming from, it’s so much easier to flip the narrative around.

Sending you hugs.


I wrote a book called Road to $4 million ARR. In the book, I shared an inside look into how we grew Hubstaff from a “nobody” to a leading time tracking app in the world today. Get your copy.