How You Turn Maybes into Milestones

Part of the role of leadership is to make things better tomorrow than they are today. To create something new and useful. To improve systems and processes. To enhance the experiences or results for end users. To uplift communities, maybe even the world.

You are in the business of creating the future. You are an architect. You make things happen. And you do all this through and with other people.

At the buy-in stage of the conversation, you may not even be sure if the new initiative is going to get off the ground, so in a sense, you are having conversations that motivate others towards something that might not happen at all. 

Furthermore, even if you know where you want to go, you may not see the details of how you are going to get there. You are working with emergence. Bottom line, there is a lot of uncertainty and unknowns. At this point, enrolling somebody in a preferred future, you are talking about maybes.

During the buy-in conversation, you aren’t asking anybody to do anything yet, other than engage in a dialogue about a preferred future and how they might contribute to it. It’s kind of a thought experiment, but it’s a thought experiment that could lead to application, so it has implications.

At this point, what matters most is inviting and supporting an attitude of openness, positivity, creativity, and willingness.

Often, leaders move to transactional conversations too early. That’s when you jump right into asking somebody to do something, and it’s a bit of a bolt from the blue. It’s putting the cart before the horse.

If the other person doesn’t have any background on what you're asking them to do, why it matters, and why this has landed at their feet, you’re likely to get some resistance.

Making one big shift matters more than any other when enrolling somebody. The big shift you need to make is from all about you to all about them. 

When you dive into a transactional conversation, this is more about your agenda and what you want to happen. Or perhaps what you believe is best to happen. Your intention could be 100% for the greater good, but that might not be how the other person is experiencing the exchange. You haven’t taken the time to enrol them first, and they are likely to feel unseen and unheard. 

When you want to enrol someone, you need to make the flip! When you flip from all about you to all about them, you consider who they are, their voice, and their talents. This is about being more interested than interesting. More interested in their skills and abilities, what drives them, their strengths, and what their contribution might be. It’s about what they see and what they might offer.

Being interested in the other person and what they have to say needs to be genuine. Most people immediately know if somebody is being disingenuous or manipulative. Ultimately, people choose to be motivated. A leader can include the right ingredients for the best outcome and create favourable conditions. However, fundamentally, the choice to buy-in or not resides with individuals themselves.

If you treat the buy-in conversation insincerely or as a token gesture, it’s likely to come off like a scene from The Office! You’ve most likely had experiences of drive-by compliments or misinformed praise from a boss. Token gestures and tick-box good-manager-moments! It has a worse impact than saying nothing at all. Get genuinely interested—it will pay off.

Once you have spent some time being genuinely interested in them and their contribution, it’s time to be interesting. The interest you want to create is a sense of excitement about future possibilities.  

You have a much better short game when you have a long game. Your long game (your vision of the future) both informs and brings meaning to the here and now (your short game). For you and for others. 

Often, your future is informed by your past memories, patterns of the way you have always done it. A future pulled present means making the shift from being a prisoner of past thoughts (memories) to being a pioneer of new possibility. Possibilities like: What do you want to create? What adventures do you want to go on? What results and experiences do you want to have?

A compelling vision of the future is a context for informing now. Your clear sense of a preferred future, and your ability to articulate it, invites excitement and energy from others. You can co-create together.

Good leaders understand that gaining buy-in is about enrollment. It’s about making the shift from “me” to “we,” from “my idea” to “our vision.” When you genuinely invest in others, listen to their insights, and co-create a future that excites everyone, you transform resistance into enthusiastic participation. Remember, people commit to what they help create. So, engage with authenticity, inspire with clarity, and build with collaboration. That’s how you turn maybes into milestones and possibilities into progress.