Step 17. Having Meaningful One-on-Ones (1:1) Meetings

I like to have 1:1 meetings with my direct reports every month. For you, this may be your VP of Sales or your Sales Manager. 1:1s are different than a Pipeline Review. A 1:1 focuses more on your direct report, not their prospects or customers. If you're not tuned in to the people on your team (their wants and needs) they will never reach their full potential for you. Below are my suggestions for running a 1:1 meeting. The purpose of these meetings is to: · Keep the circles connected · Improve the relationship · Help BOTH parties get better The issues to discuss: There are three types of issues that need to be discussed: 1. Ones that can’t be solved 2. Ones that YOU must solve 3. Ones that THEY must solve Topics: What’s Working – Ask them how they feel they’re doing. Then, give them some positive feedback. (TSP: Truthful, Specific, Positive) What’s Not Working – Ask them what they feel isn’t going well or could be improved. Then, give some suggestions to help them improve. Next steps – Ask them what they will do to improve and how you can help. Be careful not to take their “monkey”. Meaning, their issues should not become your issues. Feedback – Ask them how they feel YOU're doing as their manager. Ask for areas where you could improve. Then, share with them how you think you’re doing and how they could help you. The conversation needs to be open, honest, and non-threatening. “What’s working” Questions: - What are you most proud of accomplishing last month or quarter? - What are some of the wins? - What process is working well? - Do you feel appreciated for the work you do? - Do you have the tools you need? - Are expectations between us clear? “What’s not working” Questions: - Given how things turned out, what could you have done differently? - When did you recognize there was a problem? - What action did you take? - What is your plan to address this so it doesn’t reoccur? - What resources do you need? - How will we both know that the issue has been corrected? Don't take the monkey When your direct report asks you how to solve an issue, you can reply with, "I'm happy to provide my opinion. However, you are much closer to the situation than I am. I trust you. What is your opinion on how to get it done?" Summary You want the meeting to be a discussion. Close your laptop, put your phone away, and really be present to show you're engaged. Be sure there is time for both of you to discuss your priorities. Send an agenda in advance. There are people on your team who will appreciate having time to think before talking about an idea in a meeting. Random check-ins waste time. A tight 1:1 raises win rates, shortens cycles, and keeps reps focused. Founders and small teams can move beyond founder-led selling by using consistent 1:1s tied to the Sales Playbook, pipeline rules, and a weekly scorecard. Managers spot risk early, fix talk tracks, and keep forecasts real. Making your 1:1 meeting a meaningful experience and habit, will help your team perform at their best.