Essential Insight for Managers – How to Challenge Well

As a manager, there’s no avoiding it. You will, at one point or another, have to challenge someone’s behaviour at work. So how do you successfully challenge somebody on what can sometimes feel like an intensely personal level, when the way they’re performing or behaving is rocking the boat? When there’s every chance things are going to go pear-shaped. What can you do to keep the conversation on track and bring things to the right kind of conclusion?

How to challenge in way that people can receive your feedback

As a Manager, you can find people difficult because you don’t get on with them personally, they’re not doing what you need them to do, or they’re doing it in an unproductive way. The first step towards challenging someone in a positive, wise way is to be consciously impartial. It also helps to structure the problem and organise yourself before you have the conversation.

First, impartially pin down exactly what the issue is. Is it a reasonable challenge? Is it typical or out of character? Is the person not doing the job they’re supposed to, not doing it in the right way or to the right standards? Are they upsetting other people?

Next, identify the consequences, the reasons why you need to deal with the challenge. It might be an unhappy demotivated team, a deadline that’s about to slip beyond saving, one team member doing their job in a completely different way when it’s important to pull together, or a tricky working relationship that’s getting more tense by the day.

More self-examination is a good thing at this stage! Have you done everything you can to prevent it happening? Encouraged the right kind of performance, actively discouraged poor performance, made deadlines clear enough? If you’ve unknowingly played a part, acknowledging it helps you resolve the problem and keep it from happening again.

How do you feel about the conversation you need to have? These conversations can be difficult, but it’s important not to put them off because you’re worried you might get a flat denial, counter arguments and excuses, even an angry or upset response. The trick to this often lies in the planning. The better prepared you are, the more confident you’ll feel and the more effective the conversation will be.

Be crystal clear and specific

Know the facts. Be crystal clear and specific. Be equally clear about what else you need to find out. Why do you think they’re doing what they’re doing? Do you already know what’s behind it? Then make a plan to keep you on track. What are your key messages? What do you want the person to understand and take away with them? What would you like to see from them?

It’s a good idea to decide up front how you’ll check their progress, and let them know so they have a clear, practical idea about what improvement actually means. What it looks like ahead.

  • Be polite, respectful and calm
  • Build a rapport
  • Be positive
  • Have empathy
  • Explain the logic and reasoning behind your view
  • Provide evidence
  • Be concise
  • Stay relevant
  • Ask them the questions you’ve planned to ask
  • Listen and learn
  • Get them to agree to a course of action
  • Let them know what the next steps are

It’s important to follow up the initial conversation for everyone’s sake, for business reasons and for personal closure.

You might have had to give someone a tough message, but because you’ve challenged them successfully, in a positive way, they are more likely to listen and respond well. They won’t resent or feel embarrassed and humiliated by your intervention. Having challenged well, they’ll then also be more likely to actively look for ways onwards to show you how things have changed.