MSMP 62: Andy Allaway on Managing Teams

What Does MSMP 62: Andy Allaway on Managing Teams Talk About?

In this episode of Mads Singers Management Podcast, Mads interviews Andy Allaway, who manages a worldwide remote team of 30 at Empire Flippers. Andy shares his experience scaling a team from 10 to 30 people, emphasizing the importance of documenting processes for onboarding and cross-training. He discusses the challenges of managing human capital around seasonality in the business brokering business, and how he builds specialists as the team grows. Andy also highlights the significance of hiring for cultural fit and shares a favorite interview question to gauge a candidate's preferred management style.

When you hire someone who is 'really great' but who isn’t a cultural fit, it ends up badly for everyone, not just the wrong hire.Andy Allaway

Who Is Featured on MSMP 62: Andy Allaway on Managing Teams?

Andy Allaway is the guest for this episode. He comes from a sales background in the IT industry and made a switch almost four years ago to take on running operations for Empire Flippers. He currently runs a worldwide remote team of 30 from Prague, Czech Republic. Andy has extensive experience in managing teams through significant growth and scaling operations.

What Are the Key Takeaways From MSMP 62: Andy Allaway on Managing Teams?

• Documenting processes is crucial for effective onboarding and cross-training in a growing team.
• Hiring for cultural fit is more important than hiring solely based on skills.
• As a team grows, building specialists instead of generalists improves efficiency.
• Asking candidates about their best and worst bosses reveals their preferred management style.
• Seasonality in business requires intentional deployment of team resources during quieter times.

I told him that a more helpful reframe might be to ask what their best and worst bosses were like.Mads Singers

Is MSMP 62: Andy Allaway on Managing Teams Worth Listening To?

This episode is highly recommended for managers who are scaling their teams, especially from mid-size to larger teams. Andy's practical insights on process documentation, cultural fit, and adapting management style are valuable for anyone leading remote teams. The discussion on seasonality and specialist roles provides actionable strategies for operational efficiency. Overall, it's a concise yet rich episode with key takeaways that can be applied immediately.

Who Should Listen to MSMP 62: Andy Allaway on Managing Teams?

• Team Leaders
• Operations Managers
• Remote Team Managers
• Scaling Entrepreneurs

What Are Listeners Saying About This Episode?

It’s one thing to manage a team of 2-3 that grows to a team of 5-6.  It’s entirely different to go from managing a team of 10 to a team of 30.  My guest for this episode of Mads Singers Management Podcast, Andy Allaway, is someone who has done precisely that for the juggernaut known as Empire Flippers.  Andy comes originally from a sales background in the IT industry before he made a switch almost four years ago to take on running operations for Empire Flippers.  He runs his worldwide remote team of 30 from the center of Europe, in Prague.

Andy shared that one of the great strengths of Empire Flippers is documenting processes.  This makes onboarding and cross-training (to help the team better understand their counterparts in different departments) much easier.  When I asked what qualities Andy looked for in building out his team, he really stressed cultural fit, which is something I very much advocate for as well.  When you hire someone who is “really great” but who isn’t a cultural fit, it ends up badly for everyone, not just the wrong hire.

Andy also shared the challenges of managing the human capital around seasonality in the business brokering business.  It turns out that there’s a lot of activity in Q1 after people finish a great Q4 and year.  That means he’s had to be smarter and more intentional about where and how he deploys his team so they aren’t just sitting around during quieter times.  His operations staff are divided into:

• Vetting (are these quality businesses worth selling?)
• Customer service (challenges from both buyers and sellers)
• Migration (helping a buyer get rolling in his/her new business)

One of the advantages of growing his team, Andy noted, was that as the team got larger, he was able to build specialists instead of having “everybody do everything.”  And that makes sense, the skill set for vetting -- detail orientation and digging through spreadsheets -- is entirely different from the friendly and calming orientation of those in customer service.

Andy also noted that as his team grew, he wanted to improve as a manager, and he would ask potential employees how they would like to be managed.  I told him that a more helpful reframe might be to ask what their best and worst bosses were like.  They would then not only tell me about their past experiences but also indicate what kind of management style they really preferred.  If you have the opposite type of style, it won’t be a good fit.

Key Learning Points:

1. Andy talks about starting with a team of 10 (that’s currently at 30) - 3:34

2. Mads warns about the dangers of hiring Mini-Mes - 4:45

3. Andy talks about the importance of hiring for cultural fit - 7:07

4. Mads discusses the dangers of just hiring a “body” instead of hiring for cultural fit - 9:40

5. Andy shares a favorite interview question - 12:25

6. Mads offers two variations on that question - 12:51

7. Andy discusses his biggest management challenge in operations - 19:10

8. Andy discusses seasonality within Empire Flippers - 26:20

9. Mads share some tips for how remote teams can be more social with each other - 29:22

10. Mads cautions on “skip level” (below your direct reports) 1-to-1s - 34:00

Resources Mentioned:

Traction by Gino Wickman

Connect with Andy Allaway:

1. Empire Flippers