Working with People Pleasers?  Here’s how you can help them.

| 15 September 2023
People-pleasing is one of the obvious ways to get in our own way because so often it leads to resentment, frustration and overwhelm.

This article is written for you if you use a coaching approach in your leadership role and was first published in Coaching at Work magazine.

As leader coaches we often ask our team members to identify how and when they ‘get in their own way.’

It’s a well-used and easy cliché but like most good clichés it became one for a good reason.

People-pleasing is one of the obvious ways to get in our own way because so often it leads to resentment, frustration and overwhelm.

But before we speak about how to work with a people pleaser in your team, I want you to dig deep and ask yourself if you self-identify as a people pleaser. 

If so, how does that play out when you are coaching others?

Hands up – I speak as a reformed people pleaser myself.  It was often (although not always) my default position in my early leadership life. And I recognise the many ways it held me back. 

It was only when I trained as a coach 20 years ago that I recognised it, understood its origins and learned that it didn’t have to be my default position.  I’d love to say that I lost that default position easily but it took time, it took practice and it took a potential client in a chemistry session saying to me ‘I didn’t think you’d challenge me enough’ –  and then choosing another coach – to help me realise I wasn’t being as effective as a coach as I could be because I was too worried about being liked.

In my experience, people pleasing coaches are kind, caring and well-intentioned. 

They’re wonderful at support but not so strong at challenge (Often confusing ‘challenge’ with ‘confrontation,’ ‘criticism’, or ‘judgement’).

The term ‘fearless compassion’ really grounds for me what effective challenge is all about.

People pleasing coaches may avoid sharing their hunches, insights and observations – the very thing that might most evoke awareness and then enable change in their coachees –  because they don’t know what to say or they fear not being ‘nice’ or they fear upsetting them.

They may collude with what the coachee says – because it’s supportive or because they agree with her perspective – rather than help her to see another perspective or to re-frame or to dig deep into what might really be going on and then make some empowering decisions about what to do (rather than staying helpless).

I see people pleasing often in my supervision work – many versions of coaches metaphorically sitting on their hands saying, ‘this person I’m coaching is really not helping themselves, but I don’t know how to tell him, and I don’t want to offend him.’

Feedback ‘in the here and now’ – with fearless compassion – can be the most powerful way for your coachee to gain new insights on their impact on others.

From an evolutionary perspective, fear of rejection from ‘the tribe’ is what drives us.  We’ll do anything to avoid it and so ‘fawning’ or ‘appeasing’ or ‘people pleasing’ kick in when we’re trying to keep ourselves ‘safe.’
If you recognise people pleasing tendencies in your own coaching (and in life!) it’s worth taking this conversation to your next supervision session and unpicking it. 

But whether you self-identify as a people pleaser – or whether you simply want to help your people pleaser team-members – here’s what will help.

Our team members won’t always use the words ‘people pleasing.’  They’ll talk instead about feeling overwhelmed and busy and will often blame their external circumstances for that overwhelm.

Does this automatically mean that people-pleasing is causing the overwhelm?  No of course not.  But if both are true then I’d say it’s a likely contributor:

  • They’re often the ‘go to’ person for everything because they’re helpful and quick to respond so people are grateful – and it’s lovely be so valued, right?!
  • They say ‘yes’ to more work even though they are already overloaded. (They’ll often say ‘my team is really busy, so I don’t want to give them even more to do’- whilst adding a huge amount to their own workload).

Both things give them an instant ‘feel good’ hit. 

‘I’m a good person.’  Rejection and conflict avoided. No boats rocked.

But at what cost?

  • They have no personal boundaries (‘my door is always open’)
  • They say ‘yes’ to things on autopilot – and then get exhausted and resentful.
  • They avoid what they describe as difficult or sensitive conversations with people.
  • Their language in emails and conversations is often apologetic or overly deferential (notice how they talk/write to you).
  • They’re ‘Mum’ or ‘Dad’ to their team members or colleagues (interestingly I’ve said on more than a few occasions to my female clients ‘stop being Mum’ and only once have I said ‘stop being Dad’ to one of my male clients – make of that what you will!).

If your team member can say yes to most or all these things there is probably an element of people pleasing contributing to their feelings of overwhelm or helplessness or frustration.

​So how can you help?

Firstly, I don’t want to trivialise or over-simplify something that might have its origins in something complex, but I want you to help your team member to get off the starting blocks with this.

Once you’ve really heard their story, their challenges, their hopes and their fears; their context and their frustrations – without judgement or assumptions – you can ask them four key questions.

One – which of these things would you like to change?

Two – which of these things are within your own power to change?

Three – what would be the pros and cons of changing these things? (For you and for others around you). This is a particularly important question and one it’s easy to miss.  There are some perceived upsides to so called ‘unhelpful’ behaviours (avoiding rejection being one big one) and we need to enable the team member to give equal voice to those pros and the cons.  It’s only when we do that that their true fears, worries, beliefs, inner dialogue and concerns will be surfaced and explored without judgement.

Four – what might you need to believe about yourself or about others to change those things?

Five – challenge (with fearless compassion) either/or thinking and encourage AND thinking.

Here’s an example of what I mean by this:

A recent client of mine had a ‘my door is always open’ policy because she prided herself on her approachability and availability to her team; she cared about their wellbeing and ‘didn’t want to let them down.’  This looks like great leadership through one lens but of course she was exhausted and unable to focus on her own strategic priorities.

She saw things as an either/or – ‘I can either have my door open and be available and a good leader or have my door shut and be unapproachable and a bad leader.’

The question for her became ‘how can you be approachable AND take care of your own wellbeing’?  

That was a great starting point for her to think tactically about the small steps she could take to redress the balance.

None of us changes our beliefs and behaviour overnight.

But helping your team member to focus on the first small steps, and building from there, is a wonderfully empowering place to start.

P.S. I run live masterclasses on Moving Beyond People Pleasing a couple of times each year.  Drop if you’d like to get details of the next one.