Taking the lead on tough decisions

Every fortnight, I share actionable tips and insights about collaboration and decision-making, to help you lead smart and result-driven teams.

While I'm looking for my next job, I've been reflecting on my past roles leading teams. Certain moments stand out as the most fulfilling. Interestingly, they all seem to fall into three main categories:

1?? Intense collaboration with my team, and having fun while working together

2?? That final push to get an important initiative across the finish line and seeing the product of hard work in the hands of customers

Often, these two overlap. It feels great to go into battle together and celebrate a shared achievement. These are the moments that build strong relationships and trust.

Then there’s the third category, one that surprised me:

3?? Tough decisions.

I wouldn’t say I enjoy making difficult decisions, but I do take satisfaction from them. Because they matter. Whether it’s resolving immediate challenges or making strategic choices for the business, these decisions have significant impact.

Tough decisions are also an opportunity for critical thinking and collaboration. I love facilitating that process, bringing the right people together to explore options, give feedback, assess trade-offs, and land on a well-informed choice that will be key to our success.

That said, tough decisions are never pleasant. The ones that truly matter are always challenging:

• Tactical decisions—dealing with issues like cost-cutting, handling personnel conflicts, or managing short-term crises—can be complex and emotionally taxing
• Strategic decisions involve trade-offs, uncertainty, long-term consequences, and impact on people. If you’re not feeling discomfort, you’re probably not confronting the deeper uncertainties that make a choice strategic.

Every tough decision sharpens leadership skills and builds trust with your team, whether you’re new to leading or have been doing it for years. I’ve still got plenty to learn, but here’s what’s worked for me to take the leads on tough decisions:

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Let me share a difficult decision we faced as the leadership team of Made Tech’s SaaS products:

Eight months into developing Evidence, one of our Local Gov products, we were getting more and more uncomfortable. We had a working MVP that looked great and had encouraging initial feedback from prospects, but no serious customer in sight. It seemed like we were wasting time and money developing the product without traction. The product team felt lost without market and customer insights to steer their direction, and anxious about the future of the product and the team.

Yet, we hadn’t given the product a real chance. Our sales and marketing capacity was limited, with most efforts focused on another product.

We had a big decision to make. But it felt like a tangled mess of extreme options. Should we increase our investment to throw more Sales and Marketing effort on the product? Should we kill the product and let the team go??

I suggested that we split the decision to address two compounding problems:

• First, we had a clear gap in marketing capacity, which prevented us from reaching our target customers and testing market fit ?? We had to figure out how to fill this gap.
• Second, while addressing the marketing issue, we couldn’t keep pouring effort into developing a product we couldn’t test effectively ?? We had to decide what to do about Evidence and its product team.

That suddenly made things clearer and more manageable.

Learning #1: Breaking down big decisions makes problem-solving easier and leads to better solutions.?

There’s often a way to decouple parts of a decision and treat them with some degree of independence.?

I say “some degree” because they could still influence each other and it’s important to keep that in mind. For Evidence, if we had decided not to invest in marketing, it would have limited our options for the product. Similarly, if we’d killed the product, we wouldn’t have invested in marketing at all.

But tackling both problems simultaneously would have overwhelmed us with too many variables and too large a group of stakeholders. Splitting the decision allowed us to focus on each problem with a smaller, more relevant group of people, and explore more nuanced options on each side of the situation.

You can use my suggestion for a simple method to break down big problems into manageable issues (including a free Miro template).

Once we’d split the decision, we spent time framing each problem clearly. It was crucial to make the situation crystal clear for everyone we needed onboard, especially senior executives who had not been closely involved throughout the development and launch of our products and had the last word on our investments. We couldn’t rely on our implicit knowledge. Any ambiguity would have derailed productive discussions and led to poor decision-making.

Learning #2: Framing decisions by writing a clear summary of the problem and context ensures everyone is on the same page and ready to explore solutions.

I use a simple template to frame important decisions, that answers essential questions:

• Why is a decision needed? What’s the problem? What’s at stake??
• What are the target outcomes??
• What forces in the environment do we need to contend with?
• What criteria will drive our trade-offs?

Writing this summary, with full sentences and structure, helps us clarify our own understanding of the situation as much as everyone else's. If it’s hard to write, we’re likely missing missing a piece of the puzzle. That's one of the reasons I’m a big advocate of writing more in our jobs.

Along with framing the decision, I also identify who needs to be involved and for what input. Everyone needs to understand their role in the decision-making process.

Our two decisions about the Evidence product required different people’s consultation and buy-in.?

For our Marketing problem, we needed input from execs, as any solution required additional investment. The problem also impacted our central Marketing team and successful outcomes from the decision depended on their cooperation, so we needed their input too.?

For the product decision, we had full authority as the leadership team. However, we needed to involve the product team, as the outcome directly impacted them: depending on what options we considered, team members might be required to transfer to a different project in the company or even end up on the bench. And so we made sure to gather their input on their aspirations and preferences to inform our choice.

Learning #3: Involving the right people at the right time is far more effective than getting buy-in at the end.

You can use the decision stakeholders map above or a quick checklist to identify people who might need to be involved in a decision:

• Whose expertise and knowledge do we need to understand the situation and assess options?
• Who will authorise and/or fund the chosen course of action?
• Who will do or manage the work to implement the decision?
• Who will support or regulate that work? (e.g. The central Marketing team provided guidelines and principles for all promotional work about Made Tech that our solution would have to follow)
• Who will influence the outcomes of the decision? (e.g. successful outcomes from the decision depended on the cooperation of the central Marketing team, even if they weren't directly involved in implementing the solution)
• Who will be affected by these outcomes or have stakes in them?

From that list you can select a small group who will be directly engaged in assessing and discussing options by removing anyone who is better consulted or informed asynchronously.

Asynchronous consultation is a great way to include a diverse range of perspectives without making decisions by committee. Keeping these consultations insulated from each other (i.e. a neutral facilitator or the decision-maker collects and synthesises input privately) also helps protect individual opinions from group bias.

To be continued!

Next week, I'll share how we explored and assessed options, and how we chose a course of action and got everyone onboard with it.