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The question I need help with my career. My heart sinks every morning – I feel overwhelmed, under-capable. Everything is a firefight and I just get through and think OK, and then I must face it all again the next day, repeat ad nauseam.

I feel I’m over-promoted. Probably because of a family connection. I’m very senior at a large charitable foundation.

I feel a fraud and I have no idea how to make people do things, I just am not a natural leader in this area. I want to “like” people into doing things. I never “command”, I always almost plead – a sort of, “Please, please, if you could would you…” puppy-dog style. And it is exhausting. I am not strategically bad, on that level I think I am OK, it is all the rest.

I spend half my time worrying whether I have upset someone, said something wrong or been misunderstood; and whether I can get this or that person to like me. It is all so exhausting. I suppose this has been my philosophy throughout life. I don’t think it is a good strategy for life either, but I don’t seem to have an alternative. I feel as if I have never quite grown up. I tried executive coaching, but it didn’t work.

Philippa’s answer That’s the trouble with being a woman, we are often trained by our background and culture to be more likable than assertive. I also think it is a shame when people try a psychological therapy once and then dismiss it. Finding the right counsellor is not unlike shopping for shoes. You rarely take the first pair you see, but you try on a few and go with the best fit. Just because that coach wasn’t for you doesn’t mean every coach or therapist would let you get away with trying to make them like you. (I’m just guessing that’s what happened with your executive coaching.)

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The first thing a coach that was a better fit might tackle would be how you talk about yourself, to yourself and to others. They’d get you to change: “I am not strategically bad, on that level I think I am OK, it is all the rest” to “My strength is being able to strategise.”

Aiming for mutual respect rather than being liked will help

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If we overdo the people-pleasing it probably has the opposite effect of what we would wish because it can be annoying to be over-flattered. When we bend over backwards to get it right for the other, we often lose our ground and wisdom in the process. However, someone who doesn’t or who can’t consider an employee’s feelings or thoughts is not great either. So, like so many things, this is about avoiding the polarities and finding the middle ground.

This may make it easier to get people to do things: make everything into an “I statement” rather than a “You statement.” Avoid words like “should” and “must”. So it’s not, “You must take this report to all members of the team and get everyone’s feedback by Thursday.” Nor is it, “Please, please, please do this by Thursday thanks ever so much, please thank you.” But use the middle way which is: “I would like you to take this report to all members of the team and get everyone’s feedback by Thursday. Would that be possible?” They may say, “It’s a bit tight” and then you say, “The deadline would have to be Thursday as the grant application must be filed by Friday. What would help you meet this deadline?” And I bet they’d have an idea that could make it work.

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Aim for the space between commanding and pleading that is assertiveness.

Think about how you would like to be asked. You wouldn’t want to be asked in such a wishy-washy way that meant you didn’t know whether it was important or not. Nor would you like to be commanded as though you were some sort of robot or slave with no choice or brain of your own. If you need something done by someone, give them a bit of choice but not too much. This works outside work, too. When we are getting ready to go out in the winter we need to say to a child: “D’you want to put your coat on now or when we get outside?” Then we get better results than if we just say, “Coat on now,” or plead with them to put it on.

When you’ve practised the middle way between commanding and pleading you will feel more like an adult and this will help diminish the impostor syndrome, too. Aiming for mutual respect with colleagues rather than just being liked will also make you, and them, feel better.

The best leaders are not those who dominate, but those who listen, respect and consider feedback from employees when making a decision. I expect you already do this because even if nepotism played a part in your promotion, I doubt that is the whole story. Shop around for a book on assertiveness and maybe shop around for your next counsellor, too. I think some help to control your inner critic and impostor syndrome would be beneficial – and you’ll need that whether you decide to stay in your present role or live another life.

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If you have a question, send a brief email to askphilippa@observer.co.uk

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