world-class-one-to-ones

How to run world class One to Ones - Part 4: Challenge

This final part of our four-part series on one to one conversations is the most exciting. We're going to show you how to challenge the people in your business, push them to hit high expectations and develop them into stellar team members.

We’ve looked at building the foundations for great conversations, learned how to deeply understand people and bake supportive attitudes into your culture and your one to one conversations. Now that you’ve mastered those, you can move onto the final part of our series.

This one can be alarming: how do you challenge a member of your team to do be the absolute best versions of themselves and set the highest possible standards across your company – without coming across as a dictator?

However, if you get this right, I believe that this is easily the most enjoyable element of leading a team. This is where change occurs, where growth happens, and it’s what gets me out of bed in the morning.

The good news is that if you’ve managed the first three parts of this series, you’ve removed a huge amount of risk already. Good conversational foundations, a deep understanding of someone and a supportive attitude drastically reduce the chances of someone feeling like you’re challenging them unfairly.

That said, there are some specific behaviours which can make the challenges you make to people more productive. In many ways, this last part is the most important in the series: this is what all the previous three parts were building up to… so don’t quit now!

Here’s what you need to do:

Set expectations for the behaviours you need

Challenging someone to improve out-of-the-blue will seem unfair. Instead of just launching into demanding someone improve at something, you need to build a robust set of expectations. You’ll then be able to use these expectations as a basis for the specific, individual challenges you lay out for people in your one to one conversations with them.

Here’s how you build the right set of expectations:

  • Get consensus. Developing these expectations should not be a top-down experience: there should be input from everyone.
  • Build them into your language, and the language of the company. If your expectations are clear and practical, it shouldn’t be hard to fold them into the conversations you have on a day to day basis.
  • Review them regularly. Small companies change – a lot. If your expectations aren’t able to change, you’re going to find yourself in sticky situations when the needs of your business change. Build a strong review process.
  • Make them specific and action-oriented. Vague, philosophical expectations don’t help anyone. Your team should be able to know with certainty when they are and are not living up to them.

At Charlie, this process resulted in us defining what “high performance” looked like. We boiled down the behaviours and mindset we wanted to see in our team members to four key areas.

Get specific

Setting these expectations is all well and good – but these are usually general requirements, and feedback thrives on specifics. You’re often going to find yourself going into a one to one conversation with specific pieces of feedback in mind.

This is absolutely fine, but the most effective feedback you can give will relate to your expectations. It’s a valuable exercise to think through the feedback you’re going to give, and try to link each individual point to one of your expectations. If there’s something that just won’t fit, then something’s wrong: it’s either the wrong bit of feedback, or you’re missing a crucial goal.

In your conversations, linking the feedback and the wider expectation improves your chances of producing real change in a team member. Individual pieces of advice like “I’d like you to try not to have your phone on in meetings” aren’t particularly inspiring. When giving this feedback, I would make a point of linking it to one of our expectations: “Give Energy”. This makes the feedback feel more justified and provides a stronger incentive to the team member.

Live it at the top

People do not like hypocrisy. Challenging someone to live up to an expectation which you don’t live up to yourself is an easy way to make someone extremely frustrated.

If you want your one to ones to be successful, you’ve got to make sure that you’re living up to the expectations you set during every hour you spend with your team.

To do this:

  • Ensure everyone in a leadership position understands that the spotlight is always on them.
  • Publicly own any slip-ups you have: people are going to notice anyway.
  • Focus on the little things. Don’t be late, don’t miss meetings, don’t get distracted, don’t miss deadlines. These might seem trivial, but they’re often the most noticeable parts of your behaviour.

However, you will eventually have to challenge someone in an area where you know that you are personally weak. When this happens, you can prevent frustration building up by being as open as possible: discuss your weakness, explain the struggles you’ve had and the problems it has caused, and talk about the strategies you use to tackle your problem.

Give honest and candid feedback

This one is hard. It’s going to take up a good chunk of your emotional and mental energy, but it’s worth it.

Change and growth always requires honest and candid feedback. As a leader, you are responsible for talking to people about their behaviours and mindsets that they aren’t necessarily aware of.

  • Know how someone likes to receive feedback. Some may want it face to face, some may want it in writing.
  • Use a framework that makes it easier for you – I’m fond of SBI: Situation / Behaviour / Impact.
  • Be as honest and blunt as possible. Sugar-coating things makes people feel patronised, or can fail to get the point across.
  • Be quick. If you come up with some feedback, share it quickly. This can be risky and can lead to overly-reactive, first-impressions feedback, but if you’ve committed to the principles we laid out in Part 3: Support, then this won’t be a problem.

Appendix: Take care of yourself

All of this can come at a cost. Truly committing to developing your team and deeply engaging with them in frequent one to one conversations can be exhausting. I’ve seen it take its toll, both on other founders and on myself.

If you want to continue being a supportive and positive influence on your team in the long run, you need to build a set of strategies for looking after yourself. These will be different for everyone, but some of the things I’ve benefited from have been:

  • Learning to detach. Having your mind stuck in business affairs at every hour of the day is simply not good for you. Forcing yourself to take some time when you don’t think about work at all takes practice, but is well worth it.
  • Have your own one to ones. Find someone you trust and book out regular times with them for your own support, guidance and development.
  • Know the things which have a positive impact on your emotions. It could be exercise, cooking, reading, walking – learn what improves your mood, and make sure you get enough of it.
  • Don’t be afraid to work with a professional. I see a therapist every week – not to deal with any specific mental health issue, but more as a preventative measure. It keeps me aware of my mental state, and has helped me immeasurably over the years. I still see a worrying amount of people assuming there is some big taboo around visiting a therapist – don’t let yourself fall into this attitude.

You’re all done! Thanks for sticking through – we know this has been a long read, but we genuinely think these lessons are critical for anyone running a business or managing people, and worth the time investment.  

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