The CEO's Playbook: How to Have Hard Conversations with your Creative Team
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:
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 that’s valuable each time you connect with your colleagues, it will show. To increase your curiosity, both CEOs and creative teams can ask these questions ahead of and during conversations:
What’s something I know this person (or team) knows much more about than me? What expertise have I seen them demonstrate in the past that could help inform the final decision?
What progress have I seen since the last time we met to discuss this initiative/project/strategy/plan and where do I need to better understand this particular leader (or team’s) perspective?
How am I most likely being experienced right now? Am I actively helping to increase the level of safety, openness, and connection with this leader (or team) or am I detracting from those things?
Seek the clear path (not the correct one).
Sometimes, even with the best of intentions, we become the problem. Executive leaders get to their positions because they’ve had lots of practice making decisions and trusting their own opinions. Oftentimes, they can get stuck in their own heads and have trouble getting out of both their own way and their team’s way.
The goal for every conversation should be to advance the work. Effective meetings end with everyone having a clear understanding of what must happen next, who is responsible, what success will look like, and how the group will hold each other accountable. And it’s best when this is both captured in written notes and via video recording, so anyone who needs to can reference it later.
Be prepared that there often isn’t a single correct way to execute a creative project, but there may be a way that is best for the organization and that balances the needs of the team. You may not get exactly what you hoped for in every conversation. But with a willingness to compromise, you will see better outcomes. When the conversation starts to get tense (as it sometimes will), take a deep breath and try asking yourself these questions:
Am I clear on what the vision and expectations are for success?
Is the tension I’m feeling the result of being unclear or disagreeing that this is the right way to do things?
Where can I seek compromise so that we can all keep moving forward?
Step carefully and courageously into the discomfort.
There’s a reason 70% of workers are actively avoiding tough conversations. But it’s costing them and their organizations. We can all do better if we decide to embrace the hard stuff instead of running from it. 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. And it’s often best when the person with the most power and authority takes the lead.
The benefits of being courageous can far outweigh the risks. But our courage in tackling hard things must be matched by the necessary level of carefulness required to navigate the complexity of the situation. So before jumping into a hard conversation, maybe stop and ask yourself the following questions:
What’s the level of relational trust that I’ve built with this leader/team?
Do they have evidence that I care about them as people and care about the experience they are having in our collaboration?
How can I be more careful and intentional about how I approach the conversation to help ensure a better outcome?
The hard work is almost always "heart" work. It's not easy to notice our own patterns and then make adjustments. By deepening your curiosity, a focusing on being clear versus being right, and balancing carefulness with courage, every dollar you invest in your creative team and initiatives will go much farther.
Purple Haus is a boutique executive communications and creative intelligence consultancy that partners with inspiring leaders to realize their greatest impact and influence. Let's work together to achieve breakthroughs in your company and society.