The CEO's Playbook: How to Have Hard Conversations with your Creative Team
by Danielle Kristine Toussaint
According to a study by Bravely, 70% of people actively avoid difficult conversations at work across every level of the organization. And the estimated economic impact of avoiding conflict may shock you. The same study found that “every single conversation failure costs an organization $7,500 and more than seven work days.”
Most of us have heard the saying, “time is money.” The difference is that while there’s always more money to be made, time eventually runs out. Learning how to have tough conversations can be transformational for organizations. In our experience, few places are as ripe for misunderstanding, frustration, and avoidance than discussions between executives and their creative teams.
Here are a few tricks we use at Purple Haus to help prepare executives and creative team leads to talk about the hard stuff and avoid negative impacts to their bottomline:
01
Start With Curiosity
If you already believe you know the answer or already know what the outcome of the conversation will be, you will have exactly zero incentive to engage in a meaningful dialogue. Your resistance will show. The tension will grow with every word, every question. It will feel especially deflating for the person with the least power in making the final call. On the contrary, if you genuinely believe that you will learn something valuable in every interaction with your colleagues, that, too, will show. To increase your curiosity, ask yourself:
What’s something I know this person (or team) knows much more about than me?
What can I do to better understand the perspective of this leader (or team)?
How am I helping to increase the level of safety, openness, and connection in word and action?
02
Seek the clear path (not the “correct” one).
Even with the best intentions, we might still become the problem. Executive leaders get to their positions because they’ve had lots of practice making decisions and trusting their gut. They can get stuck in their own heads and have trouble getting out of the way.
To avoid becoming the roadblock, executive leaders should remember that effective meetings end with everyone having a clear understanding of what to do, who is responsible (and by when), how the group will hold each other accountable. It’s never helpful to share opinions that could derail the conversation or demoralize the team.
You may not get exactly what you hoped for in every conversation, so stay open to compromise. When the conversation starts to get tense (as it sometimes will), take a deep breath and try asking yourself:
Am I clear on what the vision and expectations are for success? Do I need to provide that clarity?
Do I feel tension because I’m confused or because I don’t agree about where we’re headed?
Where can I seek compromise so that we can all keep moving forward?
03
Step carefully and courageously into the discomfort.
There’s a reason 70% of workers are actively avoiding tough conversations, but doing so comes at a high cost. There is a better way. From what we’ve seen partnering with CEOs and teams in dozens of organizations, it really only takes one person to shift the direction of a conversation when they do it with care, respect, and tact. It’s often best when the person with the most power and authority sets the tone.
The benefits of being courageous outweigh the risks. To get the best results, though, we need our care for others to be equal to our courage in hard conversations. Before jumping in, maybe stop and ask yourself:
How much trust have I built with this leader (or team)?
What evidence do they have that I care about them as people and about what they have to say?
How can I best contribute to a positive outcome in this conversation?
Hard work is almost always "heart" work. It's not easy to notice our own patterns and then make adjustments. To make hard conversations easier, deepen your curiosity, focus on being clear not being right, and bring as much care to the interaction as you bring courage.
