Helping Others Make Difficult Decisions

I’ve had to make a lot of hard decisions in my career and in the past few months, they’ve only accelerated. I think I’ve become pretty good at thin slicing an issue and driving toward execution. Some of my most rewarding decisions actually are not the ones that I’ve personally made, but rather the ones that I have helped others make.

I know how hard it can be starting out as a leader and being faced with a big decision that may have consequences if not made well. Hard decisions actually are hard and they are even harder when you’re new in leadership. That’s why I am so proud when I see emerging leaders taking on difficult decisions.

There is an art to making tough decisions and executing on them. As leaders, it’s our responsibility to help others navigate these decisions, get comfortable being uncomfortable and take action themselves. It’s a skill that all leaders need to build, but they don’t have to do it alone.

Here are a few ways to help others make difficult decisions:

  • Identify the next step to move toward a decision.
    When making a big decision, all the variables and complexity can overwhelm even the most astute professionals. A key role leaders play is bringing clarity and helping individuals think in terms of “now” and “next.” You do not need to map out everything at once. Focus on what you can do now and the next action step to take while holding yourselves accountable to progress.
  • Establish a deadline.
    We can have a tendency to delay making a hard decision. We want to take the time to understand the options and outcomes. In most cases, I find that leaders at all levels benefit from having a timeline for when a decision should be made. We may even need to create a sense of urgency, beyond the traditional quarters or fiscal year.
  • Use data effectively, not as a default.
    Accurate data can dispel feelings in decision-making and assist in identifying the need for, and implications of, a decision. But data can also be a trap that drags out a necessary decision. Data should help frame and even expedite a decision, not convolute it. We’ll never have all the information we need to make a difficult decision. If we did, it probably wouldn’t be considered difficult.
  • Set targets with timelines for execution.
    Making the decision sometimes feels like the easy part once you consider what it takes to actually execute on it. That’s where the action steps, targets and timelines need to be clear and assigned for accountability. Don’t miss this step. Or you’ll put a good decision in jeopardy.
  • Check in.
    This is my favorite part of coaching others through difficult decisions. It can feel informal and even conversational while being very effective in understanding what progress has been made. I like to start by restating the goal, sharing my specific observations as appropriate and then asking for an update. Depending on the results, I may schedule a more formal reporting session with a team. This can drive progress and when needed, get it unstuck.
  • Gain buy-in.
    We rarely make decisions alone, especially the hard ones. We should engage key stakeholders to gain feedback and assess the sponsors and anti-sponsors. The key is to mitigate the anti-sponsors and bring the team together to achieve the desired outcome.

Even with more experience, difficult decisions don’t get any easier. But we can get more comfortable making them and help others feel more comfortable, too. Good leaders support others in the decision-making process and should never be anti-sponsors. When we help others make good decisions, we all look better.

We recently talked about making difficult decisions on our Let’s Tech podcast. Listen now to hear our executives share some of the hardest decisions they have had to make and best practices for navigating them. Subscribe today so you don't miss future episodes. Learn more at

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Topics: Leadership, Leadership Team