Stylist Extra The Honest Boss

“I’m a people pleaser at work and it leaves me overwhelmed – how can I change this?”

Stylist’s new columnist gives her straight-talking careers advice on everything from toxic colleagues to hybrid working.

“I am such a people pleaser at work; I always have been, but it’s to my own detriment. My auto-response to everything is: ‘Yes, sure –no problem.’ Then I become overwhelmed. I don’t know how to say no without worrying that my boss and colleagues will think badly of me for it. How can I change this?” Emma*, 27, works in finance 

You’ll be pleased to hear that as a former boss of lots of different personalities, I am a great fan of the people pleaser. Truth be known, I was probably one myself but lacked your self-awareness to pin a label on it. To me, your behaviour says you’re someone who makes life easy for others and bursts with enthusiasm along the way.

However, your eagerness could be seen by some colleagues as going above your pay grade to curry favour with the boss. There is also the possibility that, if there are lots of extra projects to do, there may be a genuine need for more staff and your keenness is covering up this fact and irritating others. I don’t think you should worry about this for now, though, as within most offices there are always legitimate extra duties that require a hungry volunteer. 

And from a boss’s POV, a “can do” person describes a perfect team member. Your positive attitude can provide you with opportunities to encounter colleagues outside your own department who you might normally not have much to do with. It’s an easy means of networking, building useful allies for the future and picking up new skills as you go. 

Yet, as you’re discovering, being an eager beaver can land you in trouble as you might not always have the capability to complete what’s required. If you say “yes” automatically to doing something, but end up not doing it properly or completing it late, you risk double jeopardy. Your initial willingness could see you nosedive from being appreciated to  being frowned upon. Plus, your failure to deliver could have damaging consequences for the boss. 

More experienced colleagues will think you should have known better. These are the sort who stay in their lane and expect others to do the same. My advice is not to be overly intimidated by their lacklustre example. It can actually be helpful to a boss when an enthusiast on the scene ruffles older feathers. It encourages a team to evolve and ensures that habits don’t become stale.  

Throughout my leadership years, I have always chosen to appreciate the positive attitude of the person who thought for themselves and didn’t worry about upsetting the status quo. I remember one colleague, who was in his first job on my team and was entirely instinctive and full of enthusiasm. He used to burst into my office without an appointment simply because he’d suddenly had a brilliant idea. He bypassed my PA every time, ignoring the time-old hierarchy of suggesting his ideas firstly to his own line manager. And I loved him for it! I chose not to worry about the seething from his more experienced colleagues. 

They judged him to be some sort of cheeky upstart who had the nerve to ignore the traditional office etiquette by approaching me without any nervousness or usual decorum. I was delighted he broke these so-called rules. I found I was stimulated and energised by those like him who were willing to do something outside of their job description. These were often the people who had a different way of tackling a problem and weren’t afraid to challenge me. Office politics are something you’ll learn to navigate, but most of the time, they are generally best ignored.

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Of course, the downside to a willing attitude, as you have discovered, is when you’ve volunteered for something only to discover that you’ve taken on too much. In future, tone down that auto response by learning to ask some key questions about the task before committing to it. It’s a matter of establishing the scale of the workload and adapting your reply accordingly. So, you learn to ask something like: “Is there any wiggle room on the deadline?” or “How long would you normally expect this to take?” and “Are there any shortcuts you can recommend?”

Then, if it’s plainly obvious that you can’t possibly manage the task in time, you can respond with: “I can definitely do XYZ and perhaps someone else can pick up the rest?” This means you are still seen as willing but, most importantly, you know you’ll be able to deliver. Your boss should be pleased with your ability to analyse what is required and, because you’ve been so logical and unthreatening, some colleagues will be encouraged to muck in alongside you. 

I have known and encouraged many people pleasers throughout my career and they have justified my loyalty by enjoying brilliant careers and eventually becoming the boss themselves. Their success is truly down to being like you: someone determined to please. That young “upstart” colleague I described is now a leading player on a global brand. Learning to silence your auto response is a skill that will enhance your ability. It’s a simple matter of training your brain to think before speaking. Meanwhile, don’t let your regrets of being overwhelmed dampen your innate hunger. I am confident that with some key tactical changes, you will be rewarded for your helpful nature. 

The Honest Boss has held senior management positions at some of the world’s most well-respected companies. With over 25 years of experience under her belt directing and mentoring teams of people around the globe, managing multi-million-pound budgets and representing brands on the international stage, she’s more than qualified to help sort out your work woes. So, whether you’re feeling overlooked for a promotion, struggling with being back in the office or you’ve thrown up in front of your manager, The Honest Boss is here to give you no-bullshit career advice.

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