How to have a difficult conversation

Scooterworks

Every manager has to deal with uncomfortable situations from time to time.

From giving constructive feedback to letting people go, difficult conversations are part of life.

If you’re not sitting down with a troublesome member of your team, and dealing with the stuff that’s so troubling, then you’re not managing — you’re ignoring/avoiding/ evading/bailing/hiding/running-away-from and not living up to your responsibilities.

Some of the most difficult conversations involve key players who aren’t living up to their responsibilities or your expectations; worse still if the problem is a fellow founder.

  • Deal with problems early — don’t wait for a mythical right time. Give feedback (good and bad) as near to the source as possible. Immediate and direct is better than delayed and fudged.
  • Use direct language — “you’re not pulling your weight” isn’t very helpful; “I’m really frustrated that each new feature takes much longer than your original estimate,” is.
  • Write it down — the more difficult the conversation or the more likely you are to chew over your words, the better it is to use notes. I make sure I can stay on track by looking at my crib sheet and saying “Let me make sure we’ve dealt with everything. Oh yes, …”

No amount of experience or preparation ever makes these situations easy, but leadership means entering the discomfort and dealing with the issue.

One final point — don’t tell them how difficult it is to say this stuff. You may think it helps to get them on your side. It doesn’t. If it’s hard for you to say, it’s even harder to hear – so stop thinking about yourself and try to empathise; this conversation is not about you.

Neatly filed under Leading,Managing on September 23, 2009
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5 cracking comments

Taylor Davidson on September 23, 2009 at 2:53 pm

Can we conduct a difficult conversation asynchronously?

Does it have to be face-to-face?

Does the entire conversation have to happen at one time? Is there information we should share immediately, and others we should wait to follow up on to discuss at different time, medium or method?

Curious on your thoughts, honestly it’s something I could stand to learn..

Nick on September 23, 2009 at 6:57 pm

Hi Taylor. I’ll try each of those questions in turn:

Asynchronous: simple feedback is fine. I recently worked with a logo guy, we never met, all the work/feedback took place through Basecamp. Just a couple of snafus on language (him speaking Adobe, me speaking Excel). Were any of these conversations difficult? Only one. Would it have been better face to face? Yes. Did anybody mind? Both of us, just a little bit.

Face-to-face: The more difficult the conversation the more important it is to be face-to-face. Assuming the reason for having a difficult conversation is to improve the performance of the organisation, it make sense to be as helpful and honest as possible – body language can plays a big part. Whether telling someone you’re sorry, you’re disappointed, or anything else with high emotion, looking them in the eye will underline your honesty and the point.

Having said all that, if you can’t be within whites-of-the-eyes range, so be it. But be prepared for a more protracted process.

All at once: If someone has a problem with me I like to know about it immediately and deal with it straight away. Once should be enough. However, I was working a while ago with a fella who thought I could improve the way I handled meetings. Some of his feedback was difficult to hear but changed the way I do things — a mentoring piecemeal approach was the only way.

Many difficult problems don’t go away after one conversation, but without that first one, and the commitment to deal with things, they never will.

Immediacy — as close as possible. Ideally it should be as simple as giving a compliment (you’d feel ok telling someone they look great, even if you can be overheard) but in reality it’s not. Personal conversations, and difficult ones are personal, should be between the people involved so consideration should be given to privacy. Of course, it’s easy to make something out of nothing so a bit of breathing space can be a good thing.

In general, the more difficult the conversation, the more you’ll need to prepare, the greater the benefit of body language.

The skippy way is to be honest (without being brutal), clear, prepared, and expect both parties to work towards the solution.

Taylor Davidson on September 28, 2009 at 10:18 am

Thank you for the detailed thoughts and advice. I suppose the only important thing to add is to understand the other party in the difficult conversation and to modify our approaches to use the methods, mediums and timing that fits them.

Much appreciated.

Nick on September 29, 2009 at 8:24 am

I have to agree with you. Understanding and empathy are at the heart of all good relations. Sadly, there are situations where there is no such thing as good timing (like resigning from a small company or tackling something like body odour) or an absolutely right way to deal with things, but it’s always possible to make a bad situation slightly easier with a bit of thought.

Julia Borowski on November 5, 2009 at 10:59 pm

Still being on the first couple of steps of the management consulting ladder, I’m often at the other end of these difficult conversations. Obviously been a while since you where there :) so let me share two of my thoughts:
1. The good old carrot and stick. Balance the difficult stuff with the good stuff. Be frank in your critic, but if you want your employees to stay motivated don’t forget telling them what they do excellent as well.
2. Feeling a bit stressed and edgy? When unhappy about your employee’s performance sometimes it can be worth reflecting over why you are so bothered. Is it at all possible that it’s connected with how you’re feeling or your own worries?

What do you think? ...