Jamie Webb Smith is a seasoned tech leader with nearly two decades of leadership experience across global teams in a range of technologies, company sizes and stages of growth. He is currently CTO at Numan and discusses his experience leading as a people pleaser.

Jamie Webb Smith

As a leader, you have responsibilities to your peers, team and organisation. Being an effective leader requires a spectrum of skills, and at the core is managing people and their expectations.

But as a people pleaser, your sense of self-worth is almost entirely determined by how others see you and their validation. So you have this overwhelming urge to ensure you’re meeting the expectations and needs of those around you at the expense of your own well-being. So you’ll do anything to avoid letting others down, to avoid conflict – even if it means being someone you’re not.

As a leader in tech and as a people pleaser, I’ve been through a journey of learning how to manage that part of my personality, and I wanted to share some experiences and helpful tactics. It’s helped me craft a much more fulfilling role and helped create brilliant outcomes for my peers, managers and teams. I hope it can help you too.

My experience as a people pleaser

First, to set the scene, I’ll discuss what it looked like for me as a leader who over-indexed as a people pleaser and wasn’t acknowledging it.


people pleaser

My calendar was full of meetings (and I mean full!). I had between 2-3 hours a week meeting free, that’s it. I had meetings booked in early for the team in the UK. I had meetings booked late into the evening with the US team (at this point, I’d said “yes” to being on the UK and US leadership teams). 

So my mornings were an anxious mess of rushing to start work and rushing from one meeting to the next.


My team were lost. I failed to delegate because I worried about giving them too much work and felt it was a badge of honour that my team was free. I wanted them to like me, so I kept the “messy” work on my plate. 

I didn’t realise till much later they were bored and disengaged. I was chaotic and erratic to them, randomly asking small things and not sharing the big picture or the meaty, messy (rewarding) work. Therefore, ironically, to please them, I was making them less happy.


people pleaser

I had to find time outside of ordinary working hours for the work I had to do. Because I kept saying yes to everyone, I needed more time, and my work was poorly thought through and sloppy. I was constantly worrying and anxious about all the things I hadn’t done for that day. 

My manager asked me frequently to redo work and expressed disappointment in what I had done. I often made stuff up on the spot in meetings to make it appear like I’d thought it through but decided not to write it down.


My ability to show up eager, engaged and my best self was shot. I was no longer exercising (something I had kept in my life since a teenager) and not finding activities to unwind. There was zero flow between work and life. My back was in constant pain (no exercise, no time to go to the physio) my mental health was at an all-time low. 

During this time, I frequently suffered from crippling anxiety. I was impatient and distracted with my wife and kids. I took so much of my work personally and often had nights I couldn’t sleep thinking about a meeting the next day (that I hadn’t properly prepared for).


I was miserable. I had run myself into the ground to make people happy around me. Unsurprisingly, to please those around me and ensure they validated me, I actually made them worse too.

If any of this sounds familiar, I know how you’re feeling. It’s tough. But the good news is that you can break the cycle and start climbing back out of your hole with a tiny bit of effort.

Do this first: look back and look forward

Before we start on some practical steps, one set of exercises had the biggest impact on me. If you want to start your journey, I would recommend you start with these three short exercises:

  1. Look back
  2. Look forward
  3. Look for patterns

Look back

Grab a piece of paper or open a notepad doc (the more low-tech, the better). All I want you to do is think back to your happiest times. Try and find at least 3. For each of those times, do these three things in your notebook:

  • Describe the feelings
  • Describe the situation
  • Describe why it felt like that to you at that time

Look forward

On a new piece of paper or notepad, imagine yourself sitting quietly at your kitchen table 6 months from now. You’re happy and content, and you’re pleased with the choices you’ve made in life. You’re the happiest, healthiest you’ve ever been. So really imagine yourself there (close your eyes if it helps!).

  • Write down the list of things that would have to be true for you to be at your happiest and healthiest.
  • Don’t stop writing! Just let your brain go, and write down anything and everything – the aim of this exercise is quantity, not quality.

Look for patterns

Now with those two lists in front of you, look for patterns that mean something to you. What do you spot about the times you were happiest? What’s common between that and what you need to be your happiest, healthiest self?

For me, patterns that kept coming up were:

  • Belonging: Working in a team that accepted me, where I felt I belonged.
  • Clarity: Goals and expectations were clear.
  • Trust: I had the trust of others, and I trusted them. We’d built up a trust that meant the cost of failure and also asking for help was low.
  • Confidence: I had built up confidence enough that I didn’t constantly doubt myself.

Now you have your central themes; they will be key as you look at correcting some of your people-pleasing biases. We’ll use these in the next actions as a guide to help you make some solid decisions about how to set your boundaries, say no and invest in your own self-worth.

Practical field guide

This guide is intended to provide a set of tactics to help you manage your people-pleaser biases. I recommend you try them in order, but if one jumps out first, then start there.

  1. Recognise the behaviour: This will start to build a sense of understanding. During the day, acknowledge when you put other people’s needs or desires above your own. At this stage, it’s just about acknowledging and noting the behaviour.

    Practical action: At the end of each day, write down when you put other people’s needs ahead of your own.
  2. Learn how you can say no: Practice setting boundaries and saying no when someone asks you to do something you don’t want to or can’t do.

    Practical action: Take a small action every time someone asks you to take on a task/responsibility and build from there:
    • The first step is to simply ask one question. That’s it. Just ask more about it, for example: “What help do you need?”, “When do you need it done?”, “How urgent is it?”, “Is there something specific you need?”
    • When you’re comfortable asking a single question, then start to explain what your current priorities are. That’s all. For example, “Understood, I’m currently focused on getting the team ready for the product launch tomorrow”, “Got it, I’ve got to also got to prep the group for the MBR on Thursday”. 
    • It opens up conversations about what can be moved around and allows people to understand your schedule without you saying “no”.
    • Once you’ve got comfortable with that, next is the big one — actually saying “no”. This will feel different for each of us, but if you start by asking questions and then explaining your priorities, giving them options will be much easier. For example: “I can’t help until Friday”, “I can help with this, but I can only do X”, or “Unless you can help me with X, I don’t have the time to help you with Y.”
  1. Craft your boundaries: Create the scaffolding around your time and energy to build you up independently of others. Remember the exercise on your central themes above (look back, look forward)? You can now use them to create some boundaries for yourself.

    Practical Action:
    • For each of your central themes:
      • Create a list of what would enhance and detract from that feeling.
      • Choose one thing from the enhance list and create a ritual/habit around it. Then, book it in your calendar and commit to doing it. It’s important to start with just one to build momentum.
      • Once you have one settled in, add more and more to your weekly/monthly rituals. But start small!
  1. Talk about your themes. Sharing with people around you about how you do your best work is impactful. It allows your manager to support your boundaries and energy and lets your peers better understand how to work with you best. In addition, it builds a sense of collaboration with your team.

    Practical actions:
    • Choose a single theme.
      • Spend 10 minutes at the end of your next 1:1 with your manager, asking for their help on that theme. You could start simple, for instance, “I’ve been reflecting, and I’m struggling with a sense of belonging/building trust/creating clarity. I’d like to think about how I could best <enhancers>. Can we discuss that?”
      • Spend 10 mins in each of your 1:1s with your team discussing the same theme. The aim is to help them understand that you’ll do this differently because you’re trying to invest more in one of your central themes.

From my experience, investing just a small amount of time in understanding yourself better creates a construct within which you can make slightly better decisions about how to spend your time.

As you make those slightly better actions, you’ll feel a shift, and things get a little easier and lighter. The next set of actions gets more manageable from there, and you can build.

So my best advice is to start small – do the “Look back and look forward” exercise and then note the behaviour. Build the confidence from there and then go through the other practical actions.

Good luck!


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