Six tips on how to have difficult conversations

Small business has big worries. And one of the biggest ones can be difficult conversations. 

They are the ones that you recognize you should have with that vendor, employee, contractor, partner, client, or manufacturer. But instead you’ve been avoiding it for the past few days, weeks, months, maybe years. You know what I’m talking about.

But they are just part of owning a business.

So let’s talk about it. 

Last week my business partner (and one of my closest friends) came into town. And it was a treat to spend so much time with him. I took him to all of my favorite places for tacos, lobster rolls, bagels, noodles, croissants, donuts, ice cream, etc. 

During our food quest, in the back of my mind, I knew that I had to have a heart to heart with him. There were some things he did that we needed to address. But I was worried; I didn’t want to screw up; I didn’t want to screw us up. And I so badly wanted to avoid it. I also knew I couldn’t if I wanted things to operate better in our company. I decided to talk to him over donuts, a little bitterness with sweet deliciousness. 

While we sat in Donut Pub, my favorite donut shop in NYC, with the ambiance of an old school diner, and after we were presented with our apple fritter, marbled cake, chocolate glazed, and honey-dipped donuts, I asked him a direct question that addressed the issue. My tone was straightforward but not accusatory. And he knew exactly what I was talking about. 

He took it incredibly well, and I appreciated his willingness to enter into a conversation like this. It took a lot of character, humility, and grace. Maybe his reaction was a result of the beautiful buffet of fried dough before us, but I’m pretty sure it was all him. We carried on with the eating and talking as we reached some very practical and promising steps toward progress. It all felt and tasted delicious. 

No matter what the outcome, having those types of conversations are challenging. And they need to be dealt with with care. 

Here are some lessons I’ve learned over the years. 

What’s necessary isn’t always easy.

Hard conversations are hard. No one I know likes having them. We want to avoid them. But we shouldn’t. And acknowledging and accepting that they are hard is a good step forward. Avoiding these talks is a solution, but it’s a bad one. So we need to say to ourselves that we need to do this, and it won’t be easy. Somehow articulating it helps. For we need to have them no matter how we feel about it. My kid hates shots, but he needs them to stay well. If we want a healthy company, we need to give it shots of difficult conversations. 

The human component is the hardest part. When we are dealing with people, we need to consider emotions, egos, background, etc. We need to treat them with care. And business is all about people and relationships. And the healthier they are, the better your business will run. If you have bad relationships, that will only hurt your operations in the long run. And often, the best way to address those issues is through words, well-chosen, skillfully delivered, difficult words. They can be the difference between life or death in a small business.

Don’t just know it, do it. 

You may know that these conversations are necessary, but just because you know it doesn’t mean that you’ve accepted it. There are plenty of people who know that exercise is essential but still don’t work out. If you accept it, you practice entering into difficult conversations with the people around you. That doesn’t mean you need to embrace it or find it something fun or enjoyable. It’s something that we do for the good of our company and the people with whom we work.

Also I should add that you don’t need to be perfect at this, just good enough. Sometimes we can be sidelined by the urge to having the perfect words. That’s not going to work here. There are no perfect words. There are only good words.

Don’t make it personal. 

I don’t mean this in The Godfather way, when Micheal Corleone said, “It’s not personal; it’s just business.” I believe that everything we do in business is personal. When we are dealing with people it’s personal, even if the context is a company. And when you are confronting someone or providing feedback or negotiating, you shouldn’t be easily offended, and you shouldn’t go on the offensive. You definitely should not attack them personally. Instead, tell them what you believe, observe and give clear examples. The listener might not respond well. So if that is the case, it is best if you keep your cool. You don’t need to be a robot, but you don’t need to get too emotional, either. It’s better, even critical, to stay rational in those moments. The way to do that is to realize that their reaction is rarely about you. They are in a situation that they don’t like and find stressful. And in those types of moments, people can often behave poorly. Let them. But don’t join them. 

Do it sooner than later.

It’s always tempting to procrastinate, especially when it comes to confronting someone about their poor performance or behavior; but don’t. The sooner you do it, the better. That way, the action that they did or didn’t do can be fresh in both of your minds. The longer you wait, the less they (and you) will remember. Having the memory close is vital so that both parties can remember what happened and talk about it from a relatively clear perspective and not one that is faded and worn by time. 

You need to initiate. 

A lot of leaders wait to bring up issues. But that is not good. It’s our responsibility to initiate hard conversations. The business you are working on is yours, after all. We should model good behavior and create a culture where people feel like it is safe to have their own talks with their colleagues and with you. But the fact of the matter is that many of them don’t know how to. They aren’t armed with the skillset or confidence to do it. So it’s up to you, business owner, to step into the gap. When there is an issue between people, you can often tell. If that’s the case, clear the air by asking them to grab a coffee or meet. And ask them what is going on. Proactivity is key here. 

Prepare, prepare, prepare. 

Don’t take these conversations lightly. They are important. If you have employees or a team of any sort, you need to treat these moments as critical. They can make or break how a person feels around you and about the company. So it’s essential to prepare. I take notes on the things that I observe for each person. Then I crystallize it down to my main point. I try not to have more than two. But having just one is better. In these high-stress situations, keeping your communication as simple as possible is always the better route. After I’ve distilled my point, I figure out the best way to communicate it. I write how I want to frame my point: a question, a statement, a story, etc. Sometimes I’ll write out what I want to say in its entirety. That doesn’t mean that I’m going to sit there and read what I wrote to them. I’m just trying to order and visualize what I’m going to say. I’ve tried shooting from the hip in these situations, and I usually end up shooting myself in the foot. 

Hard conversations suck. But they can yield incredible fruit. When done well, they can unleash productivity and profitability. They improve the way people feel about the company, each other and you. 

So talk to each other. Be frank. But be kind. 

Hard conversations are hard. 

But it’s good business.

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