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4 Steps to master any tough conversation, improving leadership skills, team productivity, and connection.

Why Tough Conversations = Team and Business Success

Tough Conversations can be….tough.

You’re human, so you naturally shy away from discomfort. I bet you’re an expert at sweeping tough conversations under the carpet.

But that’s where the gold is! The Tough Conversations you’re avoiding can change your life. They hold the answers needed for your team and your company to be better and more impactful. Imagine waking up everyday excited to get to work, knowing your voice will be heard and valued. Imagine feeling confident to speak up for what you need and fully owning your every contribution.

One Tough Conversation can transform your workplace relationships, create more productive teams, and increase job satisfaction across the board… but only if you commit to having it.

So how do we overcome this natural tendency to avoid discomfort and grow as a team member, leader, human, team and company?

We become Tough Conversations Ninjas.


But What Exactly is a ‘Tough Conversation’?

A Tough Conversation is the one you don’t want to have. In fact, the best Tough Conversation Opportunity (let’s call it a TCO) is probably the one that hasn’t even occurred to you.

Take a minute now – what’s the hardest conversation you can imagine having at work? And with whom? What is it you’re holding back? What are you afraid to lose? When you’ve got it….keep reading….

Tough Conversations are those defining moments that literally shape our careers, our relationships, and our lives.


OK – But Give Me Examples…

Here’s a list of Tough Conversations people face at work:

  • “You need to improve performance”
  • “I need you to change your behavior”
  • “I need help (physical/emotional/logistics)”
  • “I’m not feeling supported or appreciated”
  • I don’t agree. I think we should go a different way
  • “I’m not happy in this department; I need a change”
  • “I screwed up and I’m embarrassed, and worried about consequences”
  • “You screwed up, and I want you to take responsibility for it”
  • “No, you’re not getting the project/promotion/raise”
  • “You’re fired”
  • “I want a raise/promotion”
  • “You’re micro-managing me; I need more freedom”
  • ” I feel intimidated by you”
  • “You lied”
  • “You broke an agreement”

Any of these sound familiar? Tough, right? Now, imagine having to deal with the emotions involved. First you’ve got the anxiety of what you think is going to happen if you have the conversation. Maybe you don’t think you can even ever have the conversation, so you’re frustrated about that on top of being frustrated about your work. Then you’ve got the fear of what could happen after you have the conversation. Suddenly you’ve got an upset co-worker or boss, frustrated customers, and you feel like a disappointment or a failure when you have to say “no”.

Now, this may seem bleak and torturous, but the alternative is so much worse.

What’s the Business Cost of Avoiding Tough Conversation Opportunities (TCOs)?

Avoiding Tough Conversations is horrendously expensive:

  • more conflict
  • unhappy teams
  • missed opportunities
  • disengaged employees
  • key staff quitting, or even worse…
  • sabotaging performance

…which all add up to unnecessary spending, bloated budgets and wasted resources.

Can you imagine how avoiding Tough Conversations in your personal life can impact all that? Yikes.

Avoiding Tough Conversations is horrendously expensive.

Having the Tough Conversation without skill can be even worse – sometimes even a total train wreck. This almost always creates more conflict, which gets us back to disengaged employees, sabotaged performance and people quitting.

What’s the Benefit of Mastering TCO’s?

Having Tough Conversations ARTFULLY will:

  • increase engagement
  • reduce conflict
  • increase joy/job satisfaction
  • increase self-expression
  • increase creativity
  • increase confidence
  • increase retention (people stick around because they love where they work)
  • increase productivity (team working together)
  • improve leadership skills (people stepping up)
  • grow staff personally and professionally

Let it Go or Have the Conversation?

You may be thinking “David, why do I have to have the conversation at all? Shouldn’t I just bury it? Isn’t the past just the past? Couldn’t I make things worse?”

Yes, sometimes. I believe that about 90% of what we’re burying can be of serve us as individuals, teams, companies, and countries…if we can artfully express it.

Here are three tests to let you know if you should let it go, or if it’s time to talk.

Test 1: Is this with a person I want or have to relate with over time?

If it’s someone in another department, or a friend of a friend who bugged you but you don’t see them often and don’t want to invest in a relationship with them, you might want to let it go.

I sometimes let it go if it’s not that important to me, or if I don’t think the person is likely to listen.

But even in these cases there can be lots of growth points in simply bringing it up without attachment – one human to another – and seeing what happens. After all, each Tough Conversation moves you closer to TCO Black Belt status, regardless of the outcome.

Test 2: Does this issue keep coming up for me?

If this is the first time it’s come up for you, you might shelve it and see if it comes up again. If it’s come up three or more times in your thoughts, that’s a great clue that this could be something for you to handle. Also notice if you’re complaining about it to yourself, or to others. That’s another strong clue.

Test 3: Could this conversation make a difference to my life or work? Or for someone else?

Ask yourself – “What’s really possible from this conversation?” and really think about it. You might clear the air and feel good about working with this person. You might influence policy, set a boundary, or even make a difference in someone else’s life. And then there’s the big one….the potential for more peace.

If it doesn’t pass one of these three tests, then maybe you can let it go – at least until it comes up in your mind again.

But What if We Can’t Think of any TCOs?

The mind won’t always present our Tough Conversation Opportunities to us. Our natural inclination is to subtly sweep them into the subconscious and avoid them.

So, to find our TCOs, we look to any problem we have with someone. Including…ourselves.

Here are some good indicators there’s a TCO we’re avoiding:

  • you’re angry at someone
  • you’re avoiding someone
  • you’re embarrassed or ashamed of something
  • you feel guilty or incomplete about something
  • you’re scared something will be found out one day
  • you’re scared of their reaction if you spoke the absolute truth
  • you’re worried about the consequences of the conversation
  • when you imagine the conversation, you feel uncomfortable

And the best clue of all: You don’t want to have the conversation! This is a sure sign that you’re avoiding something, and there’s an opportunity just around the corner.

A Leadership Move, and Your Effect On Others

Having a Tough Conversation is a leadership move.

It’s saying: “I’m not going to passively allow circumstances to run me. I have a say in the matter. I’ll express myself and influence the world around me”.

In my experience, being direct with people and willing to talk about difficult topics has had some powerful and indirect benefits.

Firstly, it increased their trust in me. Sometimes even if they didn’t like what they heard, they respected me for tackling the issue.

Secondly, imagine how fearless they might be once they’ve seen you set an example. Your courage can ripple out and change the world. I’ve had people say: “You know, after you called me, I started thinking. And I picked up the phone and called someone I need to talk to.”

Does it Have to Be Face-to-Face? Can I email this in? What about a video?

Well, what do you think? 😉

Unless it’s super minor, almost nothing, do not text this in.

Do not email this in.

Best is face to face.

Second best is a live video call.

Third is a live phone call.

In the room is where you have the most influence with someone.

You get huge courage points for doing this live. Particularly if they work in the same building, it’s generally best if you can be in the room with them. You have the most influence when you’re in the room with someone.

However, there is a strong case to be made for putting your initial thoughts into a video, whether or not you send it to the person.

I love to create videos on Loom (a free service), saying my side of the tough conversation. I might delete the first 3 or 4, but I get better each time. Then, once I have something that feels powerful, clear and clean, I either go have the conversation live, or I send the video as a pre-cursor with an invitation to discuss once they’ve had a chance to digest it.

The big advantage of this is you get a chance to get all your thoughts out without interruption. And if it’s a train wreck, you can re-record!

The Risk

Now I’m not guaranteeing that you or they will like the results.

In my experience, and in the experience of my clients, the outcome has almost always been positive in some way. Yet, the outcome may be even worse than you feared. Tough Conversations can lead to bankruptcy, divorce, lawsuits, prison time, or worse.

They can lead to quitting, termination, being demoted, embarrassment, or the end of a project, client relationship or alliance.

The spiritual warrior realizes this, puts truth and love above all outcomes, and takes what he or she gets with grace.

The corporate leader will risk ruffled feathers, feeling uncomfortable, strong emotion, and even a project or relationship ending, trusting that truth will lead to growth for all.

If you seem to get a negative outcome, consider this as the outcome that was meant to happen – and you had been distorting or avoiding it by holding back. Time to trust and let the universe flow where it will…

Even if it doesn’t look positive, at least you’re clearer on where you both stand, and the ‘thing’ doesn’t get to fester in the dark. As my therapist says: “Rupture and heal!”

The corporate leader will risk ruffled feathers, feeling uncomfortable, strong emotion, and even a project or relationship ending, trusting that truth will lead to growth for all.

As always, you’re fully responsible for any actions you take as a result of this post. In fact, that’s kind of the point.

If having this conversation could have legal or medical consequences, I recommend consulting a lawyer, doctor or other appropriate professional first so you know what you are dealing with.

Couldn’t It Hurt The Other Person?

It’s true you have a responsibility to speak with compassion, and to speak responsibly. i.e. Take responsibility as much as you can for what you have done, and avoid blaming.

It’s also true that no matter how compassionately or gently you share the truth – the other person may feel upset. Maybe you both will. And again, maybe that’s needed before they come out the other side.

It’s important to note that it’s very common to use ‘It might upset them’ or ‘It might rock the boat’ as an excuse for wimping out.

If you truly believe they may be damaged in some way by this conversation, please work with a coach to ensure your wording is responsible – this can make a huge difference.

Hint: If you’re still blaming or judging them in any way – work with a coach to get over it first!

4 Steps to Having That Tough Conversation!

You can download the following document for free:

Tough Conversations 4-Step Blueprint

Often the Tough Conversation you need to have isn’t with another person. It’s the one you have with yourself in the days or weeks leading up to it.

Ways to Screw Up Your Tough Conversation

In case you need some more convincing, here’s a list of common things you can do to screw up a Tough Conversation. Do any of these and you automatically increase the tension in the room and ruin any chance of that TCO ending any way but negatively.

  • Blame them: “You messed this up.” “This is your fault”
  • Disown your experience: “You made me feel embarrassed”
  • Have no interest in their view of the situation.
  • Don’t ask permission to have the conversation.

OK, now you have everything you need. Converse away!

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Post Your Story

What’s the toughest conversation you’ve ever had? Did you have a good result? Either for you, for them, or others? Share your success story (or train wreck) in the comments below!

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Get the Free Tough Conversations Blueprint!

4 Steps to master any tough conversation, improving leadership skills, team productivity, and connection.