EP265 - Why Are You Making 1:1s So Hard in Your MSP With Julie Hutchinson and Ian Luckett

In this episode of The IT Experts Podcast, I dig into one of the most misunderstood leadership habits inside MSPs, the one to one. I am joined by Julie Hutchinson, and together we explore why MSP 1:1s so often feel heavy, awkward, or avoidable, and what is really going on beneath the surface when leaders say they do not have time for them. This conversation is about stripping away complexity and bringing the focus back to clarity, trust, and leadership rhythm inside growing MSPs.

I speak to MSP owners and leaders every week who know that MSP 1:1s matter. They understand the theory. They know they should be happening regularly. Yet in practice, these meetings are often the first thing to be cancelled, rushed, or turned into task updates that add little value. Julie and I unpack why this happens so often. It is rarely a diary problem. More often it comes down to discomfort, uncertainty, and a lack of structure. When leaders are unsure what good looks like, avoidance quickly becomes the default.

Throughout the episode, I come back to a simple truth. MSP 1:1s are not about tasks. They are about people. When leaders turn one to ones into performance interrogations or reactive problem-solving sessions, trust slowly erodes. Team members become guarded. Leaders feel drained. The meeting becomes something to get through rather than something that creates progress. Julie shares how this shows up again and again in MSPs where growth has outpaced leadership capability, leaving managers unsure how to hold effective people conversations.

I also share why MSP 1:1s work best when they are treated as a leadership habit rather than a management tool. Consistency matters more than perfection. A regular rhythm creates psychological safety. Over time, people stop bracing themselves and start opening up. This is where real issues surface early, before they turn into disengagement, performance dips, or people quietly checking out. I see this constantly with MSPs who come to us thinking they have technical problems, when what they really have are unresolved people issues that better one to ones could have surfaced sooner.

A big part of the conversation is about ownership. Julie challenges the idea that leaders need to carry the entire meeting. Effective MSP 1:1s are a shared responsibility. When team members are encouraged to bring topics, reflect on their own progress, and talk openly about what they need, the dynamic shifts. The meeting becomes lighter, more focused, and far more productive. Leaders stop feeling like they are dragging information out of people and start having proper conversations instead.

We also talk openly about the emotional side of MSP 1:1s. Many leaders avoid them because they fear difficult conversations. I am very clear on this point. Avoiding these conversations does not remove the difficulty, it delays it. When feedback is withheld, frustration builds on both sides. When issues are named early, with care and clarity, relationships strengthen. The confidence to do this well comes from practice and from having a simple structure to lean on.

Another important insight we explore is that MSP 1:1s are not the place to fix everything. They are the place to notice patterns. I explain how leaders can listen for themes across multiple one to ones and then address systemic issues elsewhere, rather than trying to solve every problem in isolation. This reduces pressure on the meeting and helps leaders think more strategically about their teams and their business.

Julie also shares practical guidance on what good actually looks like. MSP 1:1s should feel human. They should create space for personal check in, professional development, and honest dialogue. When leaders show up with curiosity rather than judgement, trust grows naturally. Over time, these meetings become one of the strongest tools an MSP has for retaining good people, developing future leaders, and maintaining momentum through change.

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