Five tips to make difficult decisions seem easy

Running a business takes hard work, grit and determination.

There’s never a shortage of things to manage. However, over the past decade, I’ve learned that running a simple operating system to help with rational decision-making enables intentional focus on leading your organization to success.

Many of the toughest leadership dilemmas are the subjective, people-related decisions that call for judgment, intentionality and tact, and they’re increasingly prevalent in a climate of ongoing economic uncertainty.

No amount of data can help with the psychological and emotional reality of making these decisions. Delivering them to your team can be an incredibly isolating experience.

An act of caring

Team dysfunction costs significant revenue, as Patrick Lencioni reminds us in his book, The Five Dysfunctions of a Team. Team issues are also, unfortunately, the hardest thing to address. Nobody wants to hurt other people’s feelings or negatively impact team morale.

If we aren’t willing to have uncomfortable conversations, we are ultimately selling our vision short.

As humans, we instinctively tend to shy away from doing hard things. So in an effort not to upset people – or perhaps to make our lives a little easier – we become very good at concocting justifications for putting off difficult decisions. The trouble is, if we aren’t willing to have uncomfortable conversations, we are ultimately selling our vision short.

When we do this, we are also selling each other short. Worse still, the emotional turmoil we are trying to avoid can escalate.

While there’s no playbook for how to handle difficult situations, I often turn to Kim Scott’s Radical Candor. Scott says that turning toward tough decisions is ultimately an act of deep caring. It is how we make decisions that are balanced, and communicate them with integrity and empathy, which is important.

I love the notion that you can and, in fact, must care personally and with humanity to show up professionally.

The trouble with procrastination

"Do the hard jobs first. The easy jobs will take care of themselves," Dale Carnegie said in his best-selling book How to Win Friends and Influence People.

The fact is, as Carnegie well knew, difficult tasks are the ones we’re most keen to avoid. And when you delay hard decisions, the roots of the issue start to take hold. The deeper the roots go, the more widely the problem can infiltrate the business, affecting more people and potentially other departments. The resulting snowball effect can often be tougher to tackle than the original problem.

It is kinder to make and communicate decisions sooner. Giving people the opportunity to process change and plan properly for it is a service they deserve.

I learned this the hard way in the early days of Grizzly, where avoiding a team issue ended up costing the business to the tune of half a million dollars.

As an independent creative agency, we’re a human-services-based business, and the tough reality is that people and money are intrinsically linked. Over time, I’ve learned it is kinder to make and communicate decisions sooner. Giving people the opportunity to process change and plan properly for it is a service they deserve.

Meanwhile, demonstrating honesty and thoughtfulness opens the door to a more respectful company culture.

One view is that the path to success lies in consistently being able to do the thing that is required in that moment. For me, this bigger-picture view resonates better with me than an emphasis on doing ‘the hard things’. Deliberately and consciously doing what is required, day by day, is how we realize the full potential of what we’re trying to build as a team.

Here are five steps to make difficult decision-making seem easy.

1. Practice daily habits: Have a routine that keeps you consistent, so you are always responding, never reacting. Make full use of the data intelligence at hand, keeping simple, consistent rhythms to spot anomalies in real time. This is largely a preventative measure to catch issues before they become problems, but they will also give you the insight to make fully informed decisions when needed.
2. Engage with a supportive community: We all experience feeling stuck at times and it is important to have someone to call on in those moments. You can’t just sit on the bench by yourself. Surround yourself with the right people who keep you responsible and hold you accountable. I’m involved with executive leadership groups and have multiple mentors, as well as regular therapy. Self-motivation can be fleeting, and you need other people that keep you in the game and develop you, just as professional athletes have coaches. Friends count too, of course.
3. Keep a consistent focus: Try not to be lulled into a false sense of security when things are going smoothly. In startups, we’re all working so hard to serve our clients and deliver good work. There are moments where you need to take a breather, and it can seem like the perfect time when things are going well. What I call the ‘comfortability cycle’ can cause you to lose traction on core disciplines. In fact, when things are going well is exactly when to be more intent on your focus. Always stay in a learning mindset to avoid losing precious traction.
4. Find your ‘brave’: Bravery comes from having belief in what’s possible. If you don’t believe there’s something more for you to achieve, you’ll never strive for the best. Belief is an amazing thing; it drives you to do what can be seemingly impossible.
5. Develop self-compassion: The flip side of belief is sacrifice. The more you believe in a vision or a set of ideals, the more you’re willing to sacrifice to help it come to fruition. Taking action in the face of adversity is the leader’s job, but you won’t always know whether the decision was the right one until long after it’s made and that’s OK.

The way you approach tough calls personally is fundamental to the long-term success of your organization and will help you shape a more positive, trusting decision-making culture over time. Keep your original vision firmly front of mind and you’ll be able to make challenging decisions with courage, empathy and integrity.

Nate Spees is a San Diego-based brand strategist and CEO of design agency Grizzly, a people-first independent creative agency dedicated to partnering with adventurous brands that challenge convention, impact culture and move conversations onward. It has partnered with brands across hospitality, retail and technology. Clients include Google, Microsoft, Marriott, Hilton, AnkariFloruss and Gordon Rush.