EP243 – From Manager to Leader - Time to Upgrade Your Thinking with Ali Stewart and Ian Luckett
IT Experts Podcast with Ian Luckett
Release Date: 07/27/2025
IT Experts Podcast with Ian Luckett
In this episode of The IT Experts Podcast, I want to talk to you about something that does not get enough attention in the MSP space, over-reliance on big clients. This is not about fear mongering or pointing fingers. It is about protecting the business you have worked so hard to build and making sure it is resilient, valuable, and able to withstand shocks that are completely outside your control. Over the last few weeks, I have seen several MSP owners lose large clients through no fault of their own. Long standing relationships, solid delivery, and good account management...
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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...
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In this episode of The IT Experts Podcast, Ian Luckett and Stuart Warwick sit down to share their Reflections of 2025, looking back on a year that has been full of growth, challenge, learning, and perspective. This is a candid and human conversation, where business lessons blend naturally with life lessons, offering MSP owners space to pause, reflect, and reset as another year comes to a close. The conversation opens with a shared acknowledgement of how quickly the year has passed and how important it is to take time to reflect before rushing into planning the...
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In this episode of The IT Experts Podcast I sit down with the brilliant Heather Macdonald-Alford from Counting Creators to explore how MSP owners can move from cash flow chaos to real clarity. This is a subject close to my heart because so many great MSPs work incredibly hard without truly understanding what their numbers are telling them. Heather Macdonald-Alford brings a level of honesty, energy and practical insight that cuts through the noise and helps owners see their finances in a completely fresh way. As we open the conversation I share a...
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In this episode of The IT Experts Podcast we explore why transparency in leadership plays such an important role in creating a confident and high performing team inside your MSP. The conversation opens with the truth many owners recognise. Leaders often hold information close because they feel unsure about what to share. When you move from the early survival stage of running your MSP into a growth stage, you realise that the team need more clarity, more context, and a clear view of how the business works. This is where transparency in leadership becomes a genuine accelerator for...
info_outlineIT Experts Podcast with Ian Luckett
In this episode of The IT Experts Podcast, we explore one of the most common questions MSP owners face, how to charge more without losing clients. Ian is joined by Justin Neale from Value Alchemists, a specialist in value-based pricing who works closely with MSP leaders who want to increase margins, strengthen client loyalty and feel more confident about the prices they set. This conversation brings a welcome sense of clarity to a topic that often feels heavy for business owners, and it explains why price increases can become a natural and healthy...
info_outlineAli Stewart has worked with hundreds of businesses, including many MSPs, guiding individuals and teams to make leadership a way of life, not a job title. She explains that leadership is not something you do now and again. It is a consistent, ongoing commitment to developing people and helping them unlock their potential. This is especially important for MSPs, where many business owners are technical by background and find themselves needing to evolve into leaders as the business grows. You start as a doer, then become a manager, and before long, the success of your MSP depends on your ability to lead, delegate and inspire others.
During our chat, Ali shared a powerful distinction that really stuck with me. Managers light a fire beneath. Leaders light a fire within. It sums up the difference perfectly. Managing is about task and control. Leading is about vision, belief and unlocking the greatness in others. That is a mindset shift every ambitious MSP owner needs to make. It is not about being in charge. It is about empowering others to step up.
Ali also walked us through her four-step leadership process which starts with visioning. And if you are an MSP leader who is waiting for someone to give you a vision, think again. You need to create one for yourself and your team. It does not need to be grand or complex, but it does need to answer the question: why are we here and where are we heading?
Once that is in place, it becomes about consistency, communication and mobilising your people. That means being crystal clear on expectations and diagnosing performance challenges early. The third stage of Ali’s framework is all about development. Investing time and energy in people and helping them grow. And finally, the fourth stage is about letting go. That is where many MSP leaders get stuck.
We both agreed that one of the biggest hurdles for MSPs trying to move from manager to leader is their inability to stop doing the task. They have grown their business by being in the weeds, and now they need to build a team that can run it without them. It is uncomfortable. It feels risky. But the truth is, you cannot lead if you will not let go. And if you are the bottleneck in your MSP, it is time to acknowledge it and do something about it.
Ali Stewart offered a key insight for aspiring leaders in MSPs. Do not wait to be given the title or the role. Start acting like the leader you want to become. Model the behaviours of people you admire. Learn the skills. Invest in yourself. And be willing to go through the journey of change and development. Leadership is not about being the most capable technically. It is about being the person who brings out the best in others. It is about consistency, clarity and courage.
We also explored what high-performing teams really look like. And again, the message was clear. If your team is doing well today, that is great. But if you want them to stay high performing, you need to keep investing in them. That means regular reviews, proper recognition, meaningful conversations and showing up as a leader who cares.
Recognition, as Ali reminded us, is one of the most powerful tools in your leadership toolkit. And it is free. A sincere thank you, a moment of appreciation, and showing people they are seen and valued can have a bigger impact than any bonus or pay rise.
This episode is a must-listen for any MSP owner or senior team member who wants to create a business that works without them. If you are stuck in delivery, firefighting daily issues, or finding it hard to trust your team to take over, this conversation will help you see what needs to change. Ali Stewart has worked with hundreds of MSPs to help them make these transitions successfully, and the insights she shares here are packed with value and inspiration.
As ever, the key is to follow the process. Step out of the weeds. Develop your people. Create the space to think. And lead from the front.
If you want to learn more about her work and how she is helping MSPs and business leaders build stronger, people-first cultures, head to https://www.linkedin.com/company/ali-stewart-&-co/. There is so much more to learn from her and the tools she has developed. Or you can also connect with Ali Stewart through her LinkedIn by clicking HERE.
Make sure to check out our Ultimate MSP Growth Guide, a free guide that walks you through a proven process to take your MSP from stuck to scalable, without working even more hours. It’s 44 pages rammed with advice, insights and inspiration to help you decide what support is available to you now if you want to grow and scale your business. Click HERE to get your copy.
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Until next time, look after yourself and I’ll catch up with you soon!