Hard Conversations

In a recent article, I’ve pointed out that one of the many ways I have failed as a leader throughout my career was failing to have difficult conversations with team members, peers, and leaders.

It seems obvious as to why this is, and many leaders I know have admitted to doing the same.

There are many reasons for this I have heard and/or felt over the years:

• It’s hard to do. It’s awkward.
• I don’t want to hurt their feelings.
• I don’t want to lose them.
• I don’t want them to give up.
• They are going through a lot right now.
• I didn’t set the right expectations.
• The goalpost moved so much on this project.
• The stakeholders are being unreasonable.
• I want to remain neutral.
• I need them to like me/be on my team.
• I don’t think the mistake/error/improvement is a big deal.
• I don’t want them to not feel seen or heard.

In recent years, I thought about the concept of having hard conversations for months. I read books and watched talks by proclaimed experts in challenging conversations, vulnerability, and business success.

But all of that reading, watching, and thinking kept coming back to one common thread that I thought didn’t exist, but it was subconsciously ever-present. It was a hard conversation because of what I was risking, not them.

If I botched it, these people that I do care about would hate me or be mad. I would lose leadership capital or even worse, express the wrong thing and send them on the wrong path for improvement.

If I had to have a hard conversation, it meant I had to take a stance. And was I ready to take a stance on it? Had I done enough thinking about it? Or did I just listen to other’s feedback and was the intermediary in the exchange?

If this conversation adds to the stress this person is feeling because of life circumstances, will this be the final straw for them to become disengaged or leave? How will I be able to replace them? What will the team think?

I, I, I, I - yes, it all came back to me.

And then it clicked.?

Avoiding hard conversations was never about them, it was about who I would be, and how I would show up before, during, and after.

Because the truth is, those hard conversations if done well, are going to help them (and me) grow.

So then I flipped it. Here is what could happen if I didn’t have those conversations:

• It’s hard to let them continue on a path with no feedback.
• They could have to guess how they are performing.
• They could feel lost if they notice others’ perceptions of them with no feedback.
• They could feel so isolated or helpless that they might give up.
• They are going through a lot right now and now could have to deal with ambiguity or uncertainty.
• They won’t hear me or others take accountability for how I or leaders could have done better to set them up for success.
• They won’t know how much they have the potential to grow even in the face of adversity.
• They won’t have a leader who takes a stance for them and supports their development.
• They won’t be able to make informed decisions on if this is the right fit for them in their career.
• They could not feel seen, or heard, or that I valued the investment of time/development because I didn’t invest in the hard conversations.

And suddenly the urgency to have these conversations become one of my top priorities.

Phases of Hard Conversations

Once I realized this, I began to practice these hard conversations with every chance I got. I even did some retroactively. They often went well, and in many cases resulted in a stronger relationship.

And there are also a lot of caveats here. The success wasn’t instant, and over time I fell into a rhythm that worked for me. The phases of these conversations look like this:

1. Reflection & preparation - sometimes when you take this step, there isn’t actually a need for a conversation with the intended audience. I distinctly remember a situation where my leader came to me about the performance of someone on my team. In my preparation to have a conversation with the team member, I reflected and realized the person I needed to be giving feedback to was my leader. Their approach to the feedback, the data they used to come to this conclusion, and the initial project direction all could have led to a better outcome. So I ended up talking to them both, separately, with feedback.
2. Feedback delivery/hard conversation occurring - this is when you actually have the discussion. There’s more to this later, but we’ll keep this part short for now.
3. Follow up - not only can receiving hard feedback or having a hard conversation be draining, but it can also feel isolating, and shake the ego from time to time. That’s not to say everyone will react that way, and some people even walk away quite enthusiastically, but in any case, it’s important to show them you are still there, rooting for them, and willing to support them in any way that makes sense.

I write these phases with the workplace top of my mind, but I have applied these phases to my personal life as well. I truly feel they are equally as important. I’ve done combinations of the three, and time and time again it has come with some brief regret that I didn’t invest the time to run through all the phases.

Structure of the Conversation?

I also think there are some formulas to help with the second phase, which I have adapted from what I have learned from other leaders over the years. I’ll share the feedback version below, and keep in mind the ‘hard topic’ conversation can be quite a bit different.

Here’s what I think the actual conversation should look like:

1. I (yes me, the speaker/leader/starter) messed up. - I know this sounds counterintuitive or even potentially a trick - but it’s not. As a leader, peer, colleague, friend, whatever role you play in this person’s life, there is definitely something you could have done better. It could be setting the expectation sooner, communicating expectations better, having this conversation earlier, not expressing boundaries, being absent, or any combination of things. But I promise, even if it is small, there is something.
2. Here is what I observed based on everything I can see (data, feedback, surveys, performance, etc.) - stick to facts here. Even if what you are trying to give feedback on is behavioral, think of examples of how that behavior is demonstrated. “You aren’t collaborative,” can be demonstrated as, “showing up late to your teammate's meetings, often leaving emails unanswered for 7+ days, late on your last two deliverables, etc.”
3. Here is the impact it has - this could be anything that is relevant. Impact on themselves, the team, the clients, the stakeholders, the business. One of those, a combination, or maybe even all. Showing someone the impact can also in a way empower them. The unintended impact is it says, “You matter enough to impact someone.”?
4. Here is what I expect to change/be different in the future - the preparation phase really helps with this. I have experienced sessions that I did not prepare for, that when all was said and done I actually didn’t want them to change anything, and again, it wasn’t them who needed to change. Now I have just sent them on a rollercoaster of feedback, for no development opportunity. Be clear on how you want them to change, and how you can change, too. This should be tied directly to step 1 and step 2.
5. Plan and follow up - agree on a plan of how you both will change and a day that you would follow up by (ideally a month or less). Put it in your calendars. And if you’re a leader, put a reminder in your calendar weekly or multiple times a week for you to check in behind the scenes on their work and give them praise if it’s going in the right direction. It’s important you are invested to see this turnaround. If at the follow-up meeting, you have seen no progress, then it could be time to discuss further action (but that’s for another day.)

It seems like a lot of effort, but I have had these conversations in a matter of 15 minutes at times, depending on what the feedback or topic is, with about 15 - 30 minutes of preparation.

I wouldn’t say I have perfected this craft, but I do think it has helped me grow individuals much more quickly. As an executive leader, I have had multiple people in my divisions move into leadership, senior leadership, and executive leadership within a 3-5 year span. Most of it is attributed to the work they do, some of it is attributed to the organization’s ability to let them grow, and a small piece of it is the investment of time in their development. It’s an incredible feeling to experience, and I wish that anyone who goes into leadership has a chance to do so.

It’s taken a lot of failing, practice, brilliant minds before me to help give me feedback on where I could have done better, and soul-searching and reflection to get to this place - but I can honestly say that feedback is probably one of the most valuable experiences you can give to a team member, peer, or leader.

Have more questions about giving feedback or a specific scenario to inquire about? Feel free to email me at connect@kaylalopez.work.?