5 questions every successful leader should ask themselves when they feel stuck

‘I don’t know what I want.’ It’s one of the most common things I hear in my coaching room, and it almost always comes from the people you’d least expect to say it, the ones who’ve built a successful business that looks great from the outside. So, if you’ve caught yourself thinking it lately, you really are in good company.

I imagine you’ve spent hours (or days, if an away day was involved!) working out the values of your business. But when did you last sit down and do the same for yourself? Because the things you wanted at 25 (probably wealth, recognition and some influence) are unlikely to be what’s driving you now. It’s more likely to be freedom, meaning and purpose.

The reason you feel stuck and don’t know what you want, is because everything you’ve built is still running on the old values. Here are five questions to help create some clarity. Grab yourself a coffee and a notebook and give yourself time to explore each question.

What’s important to me about life right now?
Start by writing down as many values as possible. The first few answers will probably come quickly, but keep going even if it feels like you’re running out of ideas by asking yourself, ‘what else?’ When you’ve done this, circle about five that intuitively feel most important to you right now. These are the ones you’ll work on with the questions below.

Where am I in two minds?
In my experience, feeling stuck often comes down to two values pulling against each other. You’ll recognise this if you hear yourself saying ‘part of me wants this, but part of me wants that.’ It’s a great clue that your values have evolved and something might be out of alignment. For example, you might crave more freedom and yet still find it hard to let go of control. Or perhaps you want your work to make a difference but you’re still glued to the numbers. One I frequently see is the man who spent years working towards a supercar and now feels embarrassed driving it. Part of him is proud of what it stands for and part of him knows he doesn’t need it anymore. Go back to your five values and ask yourself whether any of them are pulling against each other, or if there is something that didn’t make the list but still has a hold on you.  Finishing the sentence, ‘part of me wants …, but part of me wants …’ will usually help shine a light on any conflict.

How much of my diary reflects my values?
Your diary is the most honest record of how you spend your time, so go to last month, and compare each entry against your values. f most of your time is going to things that aren’t on your values list, it’s no surprise you feel stuck and lacking in energy. Spending weeks on activities that aren’t fulfilling is exhausting, however well your business might be doing. Now you know what your current values are, this is a real opportunity to align your diary and commitments with more things that energise you.

What am I telling myself that’s keeping me here?
If your diary doesn’t match your values, there are probably some unhelpful beliefs getting in the way and you can hear them in the way you talk. ‘I have to be in that meeting’ or ‘I can’t step back yet.’ Say these things for long enough and your brain takes them as instructions and stops looking for another way. Which is also why ‘I don’t know what I want’ keeps you exactly where you are. Oh, the irony!  Before you berate yourself, please know that these beliefs were created with positive intent and almost certainly helped you at some point, most likely when you were building your business and everything you did depended on you.  It’s just that they could be holding you back now. So, for the next week write down every ‘I have to’ and ‘I can’t’ that you hear yourself saying and ask whether it’s still true, because the more curious you can be about what you believe, the more insight you’ll get about what’s driving you, and once you know, you can do something about it.

What’s one thing I could change in the next 30 days?
You don’t need a five year plan to get going. Go back to your list of values and choose one that intuitively feels most important to you, then look at how you can create more time in your diary to nourish it. Perhaps that’s a meeting you ask someone else to chair, one morning a week nobody can book or maybe finding a trustee role if you want more purpose and impact.  Whatever you choose, put it in your diary before you finish this exercise, so it’s a commitment and not just a good idea. None of these exercises need to be done ‘perfectly’ and I’m sure you’ll find yourself returning to the questions more than once. After all, you wouldn’t dream of running your business on a strategy you wrote at 25, so there’s no need to run your life on one either. And now you’ve started asking yourself some deeper questions, you’re already updating it. So, if you catch yourself saying ‘I don’t know what I want,’ replace it with ‘what if I did know?’ and see what your brain does with that!