#37: 5 Essential Questions for 1:1s (for Leaders)

In 2010 I became a manager for the first time.

I quickly learned that the hardest part of managing others wasn’t providing support with their work, but managing the relationship itself.

In the beginning, my meetings with direct reports were checklist focused - What did you work on last week? What are you working on next? What do you need help with?

But, as I know now, that wasn’t nearly enough. In the 13 years since, I’ve evolved my 1:1s and my style of leadership overall - I’m a combo of cheerleader, coach and advisor to my teams, not a critiquer of their work.

Managers are essential to the success of their product marketing teams - both in aggregate and as individuals. Do it well, and you can build unstoppable, highly effective teams. Do it poorly, and even the most talented PMMs will be set up to fail.

Over the next two issues, we’re taking a deep dive into the art of running and managing effective 1:1s from both the perspective of the leader and the employee (yes, the employee plays a role here too).

Along my own management journey I’ve built an arsenal of questions and frameworks to help me run successful and effective conversations. Today, let’s start by digging into a few of my favorites.

5 Questions to Bookmark for Your Next 1:1

Rituals are powerful.

They provide a sense of stability and familiarity. We know how to prepare for them and what to expect out of them.

Few rituals are as important as the 1:1 - that weekly meeting where manager and employee meet to build alignment, trust and momentum.

And the benefits of engaging and productive 1:1 meetings are clear:

💡 Engaged employees are 1.5 times more likely to contribute innovative ideas than their unengaged peers; and

👯‍♀️ Employees who have regular 1:1 meetings with their managers are three times more likely to be engaged in their work

But, the burden of engagement tends to lean heavily on the manager. Few organizations provide guidance or training for managers on leading effective and engaging 1:1s. As a PMM leader for over 10 years, I get it. I rarely received management training myself. Which is why I started a swipe file of questions I can use.

Here are five of my go-tos that I use time and time again.

1. What’s the most important thing for us to talk about today?

   I almost always begin my 1:1s with this question, and I stole it from a previous executive coach of mine. This opens the door for your employee to bring up anything that’s on their mind - from feedback on a positioning framework to guidance on managing a challenging stakeholder.

2. What is the biggest challenge you are currently facing, and how can I support you?

   This question allows you to gain insight into the obstacles your team members are encountering and allows them to request the type of support they need most. Often as a manager, we’re tempted to solve the problem on our team’s behalf. But you may be surprised to hear that perhaps all your employee needs is a listening ear or a word of encouragement.

3. In an ideal world, what would you like to spend more time on and what would you like to spend less time on?

   This is a great way to get to the root of what brings your employee energy and joy, and what drains them. While I’m not always able to shift work immediately, knowing the ideal direction of travel allows me to plan for future portfolio optimization.

4. Where do you see opportunities for growth in our current product and GTM strategy?

   Each of your PMMs have a unique perspective based on their own individual portfolios. They may be able to spot an opportunity or obstacle that others may not have noticed. This question empowers your team members to share their unique perspectives on strategy and helps to foster a sense of ownership and buy-in.

5. What is one thing you want to learn or improve over the next quarter?

   Professional development often gets lost in the day-to-day work. Keeping this conversation top of mind will allow you to not only build growth plans for your team, but also assign projects and initiatives based on areas of interest too. Don’t let this be a once-a-year question you only ask at annual review time.

CAMPER ESSENTIALS

Here’s your manager-themed packing list for camp this week:

• 📚 Reading Material: The Coaching Habit by Michael Bungay Stanier (I buy this book for all first-time managers)

• 🛒 Gear: My Holstee Reflection Cards for thought provoking conversation-starters

That’s all for now - see you next week for Part 2.

- Tamara