Inclusive leadership

What it actually takes to keep a team together (and winning)

People sometimes ask me the secret behind the results my team posted at Microsoft: 100% retention with zero attrition, a 100% “thriving” score in our employee survey, 100% Manager Confidence & Respect, and a 96% work-life flexibility score, 25% above the company average. All while leading a national technical sales team that finished FY23 at 134.5% of a $1B+ quota.

I wish there were a secret. There isn’t. There’s a rhythm, and it’s pretty unglamorous. Here it is.

1. The 1:1 belongs to them

I held bi-weekly 1:1s with every person on my team, and I protected them. Pipeline came up, of course. But the meeting was about them: what was blocking them, what they wanted to learn, and how they were really doing. When people know they’ll have your full attention every two weeks, small problems don’t become resignation letters.

2. Everyone has a career plan, not just the “high potentials”

Every person on my team had an individual career development plan. 100% of them. And I didn’t just check a box. I actively looked for opportunities for people and helped them build their brand. One team member wrote in an anonymous survey, “Thanks for taking initiative and being proactive in identifying career opportunities for me.” That’s the whole point. Leaders should be career advocates, not career gatekeepers.

3. Recognition and wellness are standing agenda items

Our bi-weekly team meetings always included recognition and a wellness check-in. We sent quarterly morale gifts and made time to celebrate wins. It sounds small. It isn’t. It tells people that they matter as humans, not just as numbers on a dashboard.

4. Honest feedback, delivered with respect

Kindness is not the same as vagueness. One team member called my honesty “blunt,” and in the same breath said it had been “key to my growth.” People can handle the truth. What they can’t handle is finding out six months later that you never told them.

5. When change hits, lead with poise and compassion

Reorganizations and layoffs happen. When they did, I led with empathy, stepped up the frequency of 1:1s, reprioritized sales opportunities so no one was left carrying an impossible load, and worked to keep disruption to a minimum. One team member described how I handled a tough stretch as “poise and compassion.” Those two words are my goal every time.

6. Flexibility is the default, not a favor

My team members had full lives outside work, and so do I. As a special-needs parent and caregiver, I know firsthand that flexibility isn’t a perk. For many people, it’s what makes work possible at all. Trust people to manage their time, measure outcomes, and you’ll get both loyalty and performance.

Retention isn’t a program. It’s the result of hundreds of small decisions a leader makes every week.

If you’re building a team and want to talk about leadership that performs and keeps people, let’s find a time. And if you’d like a talk on this for your managers, see my speaking topics.

Karen Ferrero

Karen Ferrero is a professional services and AI go-to-market executive, speaker, and neurodiversity advocate. More about Karen.

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