Does Friday Have to Wait for Certainty?

It’s Friday, overcast and raining. I’m remembering a recent conversation with an entrepreneur who told me he wished he had more reasons to smile. He was worried about how AI would affect his business.

His concern was real. When you have spent years building a company, questions about its future deserve attention. Still, I wondered whether enjoying his day had become dependent on finding answers that nobody could yet give him.

Perhaps you recognise this condition: “Once we get through this, I’ll relax.” Except that “this” keeps changing. A difficult quarter is followed by a reorganisation, then a new competitor. Apparently, the business has not read your agreement about when you get to enjoy yourself.

For the next few minutes, let’s leave the uncertainty unresolved. We can play with how we approach it.

Your Imagination Already Works Very Hard

Imagine you supply ERP software and services. A client starts introducing AI to process invoices, analyse sales and support purchasing decisions. You wonder how much of your current work they will continue buying.

You can probably imagine the consequences quickly: fewer billable hours, pressure on revenue, difficult decisions about your team. Anticipating these risks is part of your responsibility.

But eventually, you have examined the available information and continue imagining the same outcome. By Saturday morning, you have mentally revised the budget three times. You have yet to discuss the client’s plans with them.

You have gained no new information, but the threat feels more certain.

Your imagination has had plenty of time to develop the worrying scenario. How much time has it had to develop other possibilities? An unfamiliar business development idea often gets rejected within seconds. The worrying scenario receives the whole weekend.

Let’s give another possibility ten minutes. It seems a reasonable allocation.

What Else Might the Client Need?

Keep the same client and the same AI development. Suppose they automate some work and still need your expertise. What might they need help with?

Perhaps their product records contain duplicates, supplier information is inconsistent, and purchasing rules are poorly documented. Before connecting AI tools to those records, someone needs to help make the information reliable.

Perhaps they want AI to prepare purchase orders. They still need an integration with the ERP, appropriate access permissions and a clear approval process. Preparing an order and authorising the purchase remain different responsibilities.

Or perhaps they have introduced several AI tools independently. Finance, sales and operations now need help connecting them to shared processes without creating conflicting records or bypassing existing controls.

These are possible services to investigate: preparing data, connecting systems and adapting workflows. Your knowledge of the client’s ERP and operations gives you a starting point for that conversation.

The client may need some of this support, have another provider or prefer to build it internally. You now have specific questions to ask alongside your concern about losing work.

This is serious playfulness: giving yourself enough freedom to develop a possibility before judging it. You can explore an idea without promising to deliver it. You might even enjoy discovering where the question leads.

Let People Think Before They Commit

At senior level, exploring aloud can have consequences. You say, “Perhaps we could offer an AI integration service,” and a week later someone presents a launch plan. You were just thinking out loud. They heard an instruction.

After a few experiences like this, you become careful about expressing unfinished ideas. Your colleagues become careful, too. Meetings fill with proposals people can already defend.

“For the next ten minutes, we’re exploring possibilities. We’ll evaluate them afterwards” gives everyone clearer permission to think.

Someone can suggest a service without having its pricing ready. You can develop an idea you initially disagree with. A colleague can ask an apparently basic question that reveals an assumption nobody has checked.

For strategic decisions, this matters. Exploring, evaluating and committing serve different purposes. When evaluation starts too early, you may compare one well-developed, familiar option with several alternatives nobody has had time to examine.

Playfulness allows that exploration to become engaging. People can enjoy working on a difficult question together while remaining accountable for the eventual decision.

Enjoyment Can Be Part of the Work

Think of a discussion that became so interesting you stopped checking the time. People developed each other’s ideas, someone questioned an assumption, and you enjoyed discovering something together. That is an experience worth making room for in everyday business.

Serious play gives people freedom to explore within clear boundaries. Everyone knows what is open for discussion, what remains a requirement and when a decision will follow. Here are ten ways it can become part of how a company thinks and creates:

• Give the worrying scenario a competitor.  When discussing a threat, develop another plausible scenario in which the company finds a valuable role. Give both enough attention to identify what you would need to investigate. 

• Temporarily remove a familiar assumption. Ask, “If clients stopped paying for implementation hours, what else could they value enough to buy?” Explore the answers before returning to your current commercial constraints. 

• Exchange perspectives. Invite finance to describe the opportunity, sales to explain the delivery risks and operations to speak as the customer. Let people think beyond the position they usually defend.

• Design the worst possible customer experience.  Imagine how you would make buying from your company unnecessarily difficult. Then notice which suggestions sound uncomfortably familiar. Shared laughter can make an awkward issue easier to discuss honestly.

• Build something deliberately unfinished.  Sketch a service, draw a workflow or act out a customer conversation. A rough version gives people something to change together before anyone becomes attached to a polished proposal.

• Give an unusual idea a temporary supporter.  Ask someone to develop the strongest version of an idea the group initially dislikes. They can explore its potential without being expected to endorse it afterwards.

• Change one constraint and see what happens.  Suppose the service had to be delivered in half the time, or without adding another meeting. Explore what you would redesign, then assess which changes deserve further work.

• Let the senior leader ask the basic question. “Why do we actually do it this way?” becomes easier for everyone to ask when the person with the most authority can ask it without embarrassment.

• Make room for humour about your own habits.  A leader who can say, “I seem to have turned a small question into a five-year strategy” permits others to acknowledge when the discussion has become unnecessarily complicated. It is a way of taking yourself less seriously when your own habits get in the way of useful thinking. You show that your approach can be questioned, even by you, and permit the team to suggest a simpler way forward.

• Create a small experiment people want to try and a safe playground around it.  Let a team test one promising idea with a willing customer, within an agreed budget and timeframe. Leave room for them to adapt the approach as they discover what happens.

Repeated over time, these practices can make exploration a normal part of work. People learn that an unfinished idea can receive attention, a question can be interesting before it is answered, and a serious task can be enjoyable.

The leader’s response matters. If every experiment must confirm the original proposal, or every unusual suggestion receives an immediate objection, people soon understand how much freedom they actually have.

Who Brings the First Smile?

Our entrepreneur may still have difficult decisions ahead. He can also remain open to an interesting conversation, an unexpected possibility or a moment of laughter while working through them.

The same is true beyond business. A bicycle ride can be enjoyable without evidence of improvement. A hobby can absorb your attention without becoming another achievement. The bicycle is unlikely to complain about the missing quarterly objective.

 We contribute to making those experiences possible through what we allow ourselves to explore and enjoy.

These five questions may reveal where that freedom has become restricted:

• What do you allow yourself to enjoy while important problems remain unresolved?
• How much time do you give threatening scenarios compared with promising possibilities?
• What happens in your team when someone shares an idea they cannot yet fully defend?
• Where has your need to appear competent made you less willing to experiment or be a beginner?
• If playfulness had more room in your business and life, what would you be afraid of losing?

Taking responsibility for a business includes making decisions under uncertainty. Taking responsibility for our lives includes noticing how much enjoyment we keep postponing until that uncertainty disappears.

It is still raining as I finish writing. I decided to bring myself the first smile rather than ask the weather to do all the work. Perhaps that is what our inner sunshine looks like: a little humour, a willingness to explore, and the freedom to enjoy a moment before everything is settled. 🙂

If you are curious about the value playfulness could add to your business and your life, I invite you to an Executive Clarity Conversation. We can explore where your thinking has become tightly controlled, what that means for your decisions and your enjoyment, and where a little more freedom could open useful possibilities. There is a lot of room for humour in our coaching conversations, too. We can take the conversation seriously and still enjoy a good laugh together, sometimes at the familiar habits we recognise in ourselves.

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On the Same Topic

These other three articles continue the exploration of what gives leaders more room to think, experiment and enjoy life while carrying real responsibility.

The Executive Skill Behind Better Choices
How pressure can narrow your judgement, reduce your openness to other perspectives and push you towards a conclusion too early.

Innovate or ... Learn to Innovate!
How beliefs such as “we have no time for experiments” or “we cannot be seen failing” restrict the innovation leaders want to encourage.

To Have Balance or To Be Balanced?
Why having more free time does not automatically bring enjoyment, and how the way you approach work and life shapes your experience of both.