Hold still, this might hurt; tough conversations in the workplace

No one likes having tough conversations. (You know the ones I mean. When you have to be brutally honest, direct, and you know it’s going to sting a little). Whether it’s with your partner, your coach or any other significant individual in your life, there inevitably come times when you find yourself elbow deep in these awkward, difficult or grueling conversations. Sometimes it’s all three, and they never seem to run as smoothly as they did in your head, but regardless, they need to be had.

Why? Because whether you’re having a tough conversation with your partner that leads to a more fulfilling relationship, or a tough conversation with your coach that results in a better batting average, the point remains, whether we like to admit it at the time, that they all lead to growth somehow.

In business, I’ve often found that regardless of industry or size, the need to have tough conversations exists. In this new world of constant iterations and sprints, your team needs to move themselves, their boundaries and their expectations rapidly, yet, in reality, this rarely happens and so naturally, growth becomes stunted for both the individual, team leader and the company.

Why? Simple, we’re Human. And as humans, there’s a natural desire (assuming you are generally a good person) to avoid conversations that are confrontational or that could hurt someone’s feelings. But the result of being nice is achieving nothing but incrementalism, slight improvements here and there that don’t amount to much. Of course, delivering constructive criticism or pushing your team members to step up and be better than they were yesterday will always be uncomfortable, but in doing so, you begin to burrow deep into the psyche of your company.

A simple example, in your next one-on-one or catch up, when discussing a key project or initiative update, add the words ‘so what?’ and ‘why?’

  • ‘So what’ — You completed this portion and looks good, so what? What does it mean for our team, our customer, our audience? What does it mean for our strategy?
  • ‘Why’ — Why did you approach this the way you did? Why is this the best outcome? Why did you pull in the people you did? Why did you use the other resources you did?

If you can continually ask, ‘so what?’ and ‘why’ every time you arrive at a solution, more often than not, you start to notice the difference between the no sh&t initiative (the safe, obvious or ‘we’ve known this forever’ path), and the holy sh&t initiative (the one that unlocks new opportunities or ways of thinking and have the ability to substantially propel your business forward).

As a leader I always feel like I have a responsibility to challenge and develop the people I lead, whether that’s in business, with friends or on the soccer field, and equally, I ask them to do the same of me. Tough conversations will always be a part of that responsibility.

And so I do my utmost to deliver these conversations, a task I’m still learning to master, and it isn’t easy. I’ve been proverbially punched in the gut more times than I care to admit — that feeling when you know you’ve nailed the task and should be showered with praise, but instead you’re told all the things that you could have done. Once upon a time I took that criticism personally, but now I’ve learned to accept it as a gift, to learn and grow from them, which is something that should be afforded to everyone in the organization.

To do this effectively here are some things that have worked for me:

Create a safe space for these conversations. They are private things and should be treated as such. Let your people know that you’re not playing politics and nor are you looking for insider information. Create spaces that let them know you’re invested in them.

Take emotion out of it. Completely. Naturally that’s something always easier said than done, but these conversations are about growth, and figuring out how to attain that growth. Whatever hang ups, irritations or past grievances you have, leave them at the door. And if the person opposite you cannot keep their emotions at bay, honor them. Acknowledge that they might not be feeling great now but that you trust them, believe in them and wouldn’t have hired them otherwise. Just because you need to have a difficult conversation, it doesn’t mean you cannot praise or compliment along the way.

You will often have to manage up, and that means having those difficult conversations with those more senior than you, and the answer can always be found in aligning expectations because no one in their right mind is seriously going to call their boss out. But what you can do, is discuss what is expected of you, and them, and set non-negotiable touch points that holds everyone accountable to those expectations.

Work to create a culture where peers challenge one another, instead of commiserating with one another. When facing difficult conversations, the natural reaction is to complain to your buddy at work as you both have a moaning session that makes two people feel better but doesn’t push the company anywhere. And don’t get me wrong, a good whine and a moan can be necessary and heartwarming, but limit it to the first two minutes of your conversation. At the end of the day, peers should be challenging one another and working together to push each other forward.

Currently those four things aren’t happening in business. Maybe one of them is, or even two, but not all four, and the result is employees that run away to other organizations or unproductive teams that lack motivation. Or your employees running off for regular Starbucks breaks so they can discuss how annoying their boss is. None of those outcomes will help your business. They’ll always slow you down. So have the tough conversations, and have them often if you need to. You will be pushing your organization and your people forward and eventually, they’ll both thank you for it.