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One on Ones for the Win

  • Writer: Candice Hilse
    Candice Hilse
  • Dec 16, 2025
  • 4 min read

You've built the team. You run on vision. You all meet regularly to stay on top of things. If time doesn't always work out for a one on one to happen, they're all good, right? They know to come to you with questions and problems, right? Right?



The truth? Wrong. You can put yourself out there for your team, you can say you're available, and you can do the walk to engage with your team and say hello, but a relationship is just that- time invested in getting to know and communicate with each other. Without a one-on-one, you are creating a scenario where you team is required to ask for time from you. A top performer will lean into not wanting to bother you- to prove themselves by handling more on their own. A poor performer will want to avoid these interactions naturally- not wanting the microscope on their personal performance. A new report will not feel comfortable asking for time or understand the expectations of time or format.


You've got to model managing your time well enough to invest some of it in others. The best way to gather critical information about the organization and your team comes through one-on-ones.


Here are a few benefits to consider:

  • Builds Trust & Relationships: Fosters deeper connections and psychological safety, allowing for vulnerability and honest conversations.

  • Increases Engagement & Morale: Employees feel valued, seen, and heard, increasing their commitment and motivation.

  • Supports Growth & Development: Offers dedicated time for coaching, mentorship, skill-building, and discussing career aspirations.

  • Uncovers Issues Early: Helps managers spot small problems or shifts in employee sentiment before they escalate into major challenges.

  • Improves Communication: Provides a private forum to discuss challenges, brainstorm solutions, and ensure everyone is aligned on important information.

  • Offers 360 Feedback: Allows employees to give managers feedback on their own performance, helping leaders improve. Addresses blockers, clarifies expectations, provides crucial feedback (both praise and corrective), and aligns individual work with company goals.


"Great," you might say, so how do I do it? Just like any other meeting, this is not a completely organic conversation. It is important to structure the hit list of topics and work through it.


A loose template for these meetings:

  • Connect with the employee personally: knowing your team builds inherit value in their organization by showing you know them and value them as a person as well as for their contribution to the organization.

  • Celebrate wins and recognize them (they present them): not only do you get to hear highlights you might not otherwise, you get a check on whether or not they understand their piece of the business and if your goals and wins are aligned.

  • Feedback, Goals and Priorities: Keep a note going for your personal reference for each direct report of feedback and priority changes to address in these meetings. This protects from generalized feedback and ensures the employee always understands their performance.

  • Communicate: What announcements or prelaunch items do you need to share?

    • Recently, I was on a call with a key player on a team and as we discussed how the firm communicated and reported, she mentioned story from a month prior that impacted her. She was looking for someone to cover an upcoming calendar item and was informed that person had accepted an offer elsewhere. Let that sink in. She found out someone lateral to her, out of a total of 6 people at her level, left and she was not informed. While you may be shocked, I have encountered similar scenarios at 60% of my client organizations. Long story short, talk about stuff in this meeting!

  • Ask for feedback. Questions like "What haven't we covered? Where do you need more or less support from me? What are concerns you might have?" are critical for you to gain insight you might not get outside of this time. Also, this is the time where someone will discuss a relational issue, an pain point they aren't certain about how to discuss, or just a simple request that can be a game changer, so make space for it.


Your team needs your time. Not a ton of it, but they need to know when they can soak up development from you, celebrate wins with you, and get insight on how they're doing. Your position and relationship carries more weight than you think, so it's imperative to set a schedule for these interactions and stick to it.


How often? Well, team size can impact that, but my rule of thumb is one hour per month, and if they are new in the role, I start weekly and taper off. This will look different for everyone, so gauge it for your industry, workflow and type of role, but schedule and protect this time. They will model this investment with their teams, so if you prioritize it, they will. If you only discuss operations or avoid the meeting all together, they will do the same.


Short story long, make time for your team and they will return the investment in their work and preparedness in the roles to come.







 
 
 

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