Leadership Lens: Having Keystone Conversations takes the guessing out of Communication

Great leaders don’t leave communication to chance. Keystone Conversations—the essential, upfront discussions that set the foundation for strong working relationships—help leaders take the guesswork out of communication and collaboration. By openly aligning expectations, working styles and preferences, leaders can prevent ambiguity and misunderstandings and build trust.

It’s like tennis doubles. The two players must find their best game. If they don’t discuss their strengths, communication styles, and pressure triggers, they could misread each other, hesitate on crucial shots, or get frustrated when things go wrong. However, as they discover how each other plays—who excels at the net, who prefers baseline rallies, and how they handle high-pressure points—they build trust, anticipate each other’s next move, and position themselves for court success.

“The single biggest problem in communication is the illusion that it has taken place.”

– George Bernard Shaw

‘TELL ’EM’

People cannot read your thoughts. I hear things like, ‘Surely my manager should realise I need more explicit instructions and direction.’ Or, ‘I have to wait too long for updates. I should hear from a team member every day.’ -There is no right or wrong here; only preferences. But hearing this narrative, it’s clear: they have not been addressed or agreed upon.

Research illustrates the importance of explicit communication in leadership, especially through approaches such as Keystone Conversations. Leaders can prevent misunderstandings, build trust, and improve team effectiveness by explicitly stating implicit assumptions.

Michael Bungay Stanier, a well-known coaching expert, believes that the key to creating effective and strategic relationships at work is to make them safe, vital, and repairable. To achieve this, he advocates for having a Keystone Conversation with your team.

By engaging in Keystone Conversations, leaders proactively align expectations and working styles, turning potential friction into long-term synergy.

I was coaching a senior leader, Tom (not his real name) in the insurance industry last year who had inherited an intact team of functional leaders. Tom is a decisive and goal-oriented leader who expects his people to take initiative and work independently. Quickly he noticed that his direct reports were overwhelming him with reports, updates and approval requests. He was drowning in emails and messages. I asked him if he had agreed on how to work together, individually and as a team. It dawned on him that he simply expected them to adopt his way of working. He didn’t know their personal leadership styles, nor the experience they had with their former leader.

He set up keystone conversations with each of his team members, agreeing on what they expect from each other, how to communicate with each other (cadence and volume), how to give each other feedback and the approach when things go wrong. Tom also clarified his expectations and they agreed on mutual accountability.

To no surprise, Tom’s inbox stopped being flooded and his leaders started feeling empowered to make decisions and simply keep him in the loop at critical points. Turns out the former leader was a micro manager, hence the initial habit of overcommunicating.

How Keystone Conversations work:

Michael Bungay Stanier, in his book ‘How to Work with (Almost) Anyone’, introduces the concept of Keystone Conversations—structured dialogues aimed at building the best possible working relationships. He proposes five essential questions to guide these conversations:

1. The Amplify Question: ‘What’s your best?’

This question seeks to understand an individual’s strengths and the conditions under which they thrive. By identifying what brings out their best, both parties can create an environment that amplifies these qualities.

2. The Steady Question: ‘What are your practices and preferences?’

This inquiry delves into personal work habits, communication styles, and routines. Understanding these preferences helps in aligning workflows and minimizing potential friction.

3. The Good Date Question: ‘What can you learn from successful past relationships?’

Reflecting on previous positive working relationships can reveal behaviours and practices that contributed to their success. This insight can be used to replicate favourable conditions in the current partnership.

4. The Bad Date Question: ‘What can you learn from frustrating past relationships?’

By discussing past challenging relationships, individuals can identify triggers and behaviors to avoid, ensuring a more harmonious collaboration.

5. The Repair Question: ‘How will you fix it when things go wrong?’

This question emphasizes the importance of having a predefined approach to conflict resolution, ensuring that issues are addressed promptly and effectively when they arise.

You can get started with these 5 questions, but I also invite you to think of your own Keystone Conversations. What’s most important is that you have them regularly.

Don’t leave relationships to chance and communication to guesswork. Make the implicit explicit. It’s that easy.

Get in touch if you are curious how we introduce keystone conversations in our coaching programs: jessica@intactteams.com

About the Author

Jessica Schubert

Cultural Transformation & Leadership Expert

Teams, individuals and organisations face different challenges. My mission is to listen, understand and tailor learning solutions that fit your cultural and organisational goals. My steps to transform people, culture and businesses:

Conversation

Listen and understand your challenges

Consult

Suggest tailored learning solutions

Co-create

Include leaders in the design process

Coach

Deliver, facilitate and coach

Consider

Feedback and go back to conversation

With over 25 years of corporate experience and leading large teams across Europe and Asia Pacific, I understand all facets of leadership. I leverage my experience of dealing with power dynamics and organisational complexities and blend it with proven leadership models, coaching theories and adult learning principles.