A woman looking thoughtful - representing that she is about to have an awkward conversation

So, you’ve got a tricky conversation coming up. You’ve finally been brave enough to schedule it, but the thought of addressing your colleague’s stubborn attitude is bringing you out in a cold sweat. He’s not an easy person to manage.

You know you’ve been letting this go on too long. His behaviour is getting worse as you fail to tackle it, but the 1-1 is creeping closer and you’re still not sure what on earth you’re going to say.

Meanwhile, you’re getting more and more anxious.

I know how you feel. Having ‘tricky’ or what I prefer to call, ‘awkward’ conversations, is one of the most challenging aspects of being a leader. We want to be liked, after all. And it feels like you’re having a go.

I often find myself coaching non-profit leaders around this type of conversation. In recent weeks, we’ve looked at how to encourage a report to share that they’re falling behind on a project so you can help; how to request that a colleague doesn’t talk over you; and how to work with someone resenting you for getting the role they applied for.

These conversations boil down to trust:

1) You don’t trust yourself to handle it.
2) And you don’t trust the other to handle it either.

Is this inner chatter familiar?

“What if I fumble my words? What if I just can’t get my point across? What if I make it worse? What if I get emotional? What if they don’t like me anymore? What if. What if. What if.”

“What if they crumble into tears? What if they have a go at me? What if they refuse to hear me? What if they complain? What if. What if. What if.”

No wonder we put off these conversations. So many pitfalls!

Like I say, I really get it. And – the thing is, when you get over the fear and awkwardness there are so many positives.

Two women at a desk not having an awkward conversation

What if… it all worked out rather well?

– Who knows, you might get better and better at having awkward conversations, as you navigate what strategies work and what don’t work so well

– You might begin to trust that this really isn’t about having a go. Tacking poor behaviour isn’t about complaining or making someone feel bad. This isn’t about you not being a good or a nice person. You’re not telling them off or criticising. You’re just doing your job as a leader, pointing out specific things that needs to be done differently, so the other person can be more effective in meeting organisations goals

– You might start to be seen as someone who’s an expert in successfully navigating these conversations, rather than someone who lets them slip. This quickly builds credibility and trust in others’ eyes.

– You might see that actually you can handle them, and importantly, they can too. There may be the odd conversation where it all goes awry (but really, even these are learning experiences if you allow them to be)

– You might realise that if you can face down the momentary awkward moment when the issue is raised, the long-term impact of a successful engagement makes that discomfort well worth it

– It might now be super clear to the person you spoke to exactly what they could do differently in order to progress at work

– You might find that you’re no longer burdened with that horrible feeling of failure brought on by endless procrastination. (We really don’t like breaking promises with ourselves. It makes us feel bad)

– You might find you’re able to focus on more fulfilling and creative parts of your role than keeping an eagle eye on someone else’s behaviour.

Over to you

Do you know you’ve been putting off an awkward conversation? Are you imagining the worst case scenario when you think about it? Or, can you begin to look at the positives and see how the conversation would be helpful for both of you?

What next?

It’s daunting to face these things alone, I know. When you coach with me one-to-one you get my focused support on all the various challenges you face as a leader, guiding and encouraging you every step of the way. Sounds good? Register here for a no-obligation chat.


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