Let’s talk about leadership for a second. You and I both know that sometimes, making the right call isn’t black and white—it’s more like choosing between two shades of gray. You’ve probably been there before. Maybe your sales team isn’t hitting their numbers, and you’re wondering: Do I fire some of them, (or all of them) and start fresh, or do I invest more in their development? Both options have their pros and cons, and making the wrong move can set you back.
And that’s just one of many tough decisions you’ll face. Here are a few more leadership dilemmas you’re bound to encounter:
The High-Performer with a Bad Attitude
You’ve got someone who delivers results but is draining your team’s morale. Do you keep them for your revenue protection or let them go to protect the culture?
Growth vs. Stability
Your business is doing well, and there’s a chance to expand. Do you go all in and take the risk, or do you focus on strengthening what you’ve already built?
Short-Term Gains vs. Long-Term Vision
A big client dangles a high-revenue deal, but it’s going to stretch your team to the limit. Do you say yes now and deal with the fallout later, or do you pass to keep your long-term strategy intact?
How Do You Make the Right Call?
The best leaders don’t just react—they follow a process. That’s where a structured approach comes in to help navigate tough decisions.
1. Figure Out the Real Issue: Strategy, Activity, or Skill?
Before making any major moves in terms of letting someone go, ask yourself:
Do they understand the strategy? (Coach to Strategy)
Are they putting in enough effort? (Coach to Activity)
Do they have the necessary skills? (Coach to Skill)
If you’ve coached them and nothing changes, then it might be time for a bigger decision.
2. Stick to your Core Values
Every choice should align with your Core Values. Butler Street focuses on the Four Cornerstones of Success® - Attitude, Personal Accountability, Perseverance, and Habit and we encourage to use them as guiding principles. Ask yourself:
Are we reinforcing accountability, or making excuses?
Are we taking the easy way out, or pushing through challenges?
Are we coming to the table with a growth mindset and positive attitude?
Will this decision build the right habits for long-term success?
3. Manage Agreements, Not Emotions
Leadership isn’t about gut feelings or personality conflicts—it’s about managing agreements. Before you pull the trigger on letting someone go, ask: Have clear expectations been set? Have they been given a fair chance to improve and they are not getting better? If so, then the next step is clear.
4. Use AI as a Supporting Tool
AI and analytics can help you make smarter decisions. Think of AI as an assistant that helps you:
Identify performance trends and training gaps.
Role-practice and coach in the moment
Analyze team sentiment to spot cultural issues before they escalate.
Predict risks when making strategic business moves.
Check out the AI Coaches from Butler Street. We have Leadership Coaches, Sales, Recruiting and Account Management Coaches. All designed to help you make the best decisions, fast.
5. Think Long-Term, Not Just Short-Term
The best leaders zoom out and look beyond immediate pain points. Our VP of Sales, Joey Frampus, leads his team with having one foot in the present and one foot in the future at all times.
Will firing the seller(s) create more problems down the road?
With a little more focus on skill building, will you have a better chance of consistent long-term goals?
Will going toward a quick revenue opportunity take your resources off your strategy and ultimately hurt your near-term results or will it provide a test case for some significant upside future sales?
Leadership is About Tough Calls
At the end of the day, leadership is about making the decisions that allow your business and your people to grow. Sometimes that means making the hard choice now to avoid bigger problems later. And sometimes, it means investing in your team and giving them the tools they need to succeed over the long-term even though you won’t see immediate results.
The good news? You don’t have to navigate these decisions alone. At Butler Street, we help leaders like you make smart, strategic choices through leadership training, sales coaching, and AI-driven decision-making strategies. If you’re looking for a partner to help you build a stronger, high-performing team, let’s talk. Reach out today and let’s find the right solution for you.
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