The One-on-One Meeting: An Essential Tool for All Startup Founders

July 22, 2015
Some startup founders are simply naturals at being "people managers." They genuinely love talking to people and feel energized after every conversation. They have an interaction style that encourages team members to open up because they put people instantly at ease. People don't think twice about sharing their worries and burdens because they don't feel judged and know that their manager will do what they can to help.

If the above description doesn't sound like you, take heart! While few of us are born managers, there is good news: managing is a skill, and as with any skill, there are techniques that we can learn to become better at it. One such management technique that every startup leader must eventually master is the art of conducting effective one-on-one meetings with team members.

What are One-on-One meetings and why does my startup need them?

A one-on-one meeting is a recurring, semi-formal, closed-door meeting between you and a direct report. Unlike status meetings that focus on projects and milestones and tasks, a one-on-one meeting is focused on the two of you. The meeting is intended to give both participants an opportunity to talk about what's going well (and what's not!) in their working relationship.

A lot of startup founders assume that such meetings are not necessary, or worse, a waste of time. After all, "my team members will come to me if they have a problem." Unfortunately, most of your direct reports will fail to open up because they are embarrassed to bring up sensitive issues about their working relationship with you. Some employees convince themselves that they should wait until things are less stressful before they bring up their concerns. Unfortunately, the "less stressful" moment never comes when you work at a startup!

By the time you realize there's an issue brewing, it may have been festering too long, or it could have grown to the point where the situation is beyond repair. As a leader, you want to preempt these issues by giving your team members a pre-scheduled and safe venue where they can have an open dialog with you.

How do we get the most out of these meetings?

Below you'll find six guidelines that will help you squeeze the maximum value out of these meetings:

First, Decide on the Right Frequency

A general rule of thumb is to meet with your direct reports once a week and to check in with skip-level reports (i.e. the direct reports of your direct reports) every two to eight weeks.

While there may be no pressing issues to talk about every week, you don't want a direct report to have to wait a while to get a chance to talk to you. For this reason, starting with a weekly cadence is useful. You can always increase the interval between meetings if weekly proves to be too frequent. At least once a month for each direct report, however, is the minimum.

Second, Block off the Time

Fire up your favorite calendar app and make sure you and your direct reports have recurring meetings scheduled on the same day, same time every week. Start with 30-minute blocks and adjust if needed. Consider that time sacred and make sure everyone else in the company knows it. If you truly need to reschedule (say, due to a board meeting or a long-overdue vacation), send a proper email explaining why, then make sure you don't miss the next one. A manager who constantly cancels the scheduled one-on-one meeting with an employee is effectively saying, "I don't think you're important."

Third, Keep a Running, Shared Document for your One-on-One Meetings -- One Document per Direct Report

Create one document for each direct report and update it throughout the week as things come up that you know you'll want to discuss with them, even if all you add is a bullet point. Share the document with the direct report and ask them to add their agenda items as well. During your meeting, note any agreements or decisions reached in the document, and hold each other accountable by checking on the status of action items in your subsequent meeting.

Fourth, Have your Direct Report Lead the Meeting

While you may be tempted to use the one-on-one meeting as the time to give your direct reports their tasks for the upcoming week, that's not the purpose of the meeting. Instead, the meeting should mainly be your direct report's time to talk and your time to listen. Look for clues about what keeps them motivated. Learn a little more about their personal interests. Keep an eye out for signs of stress, frustration, confusion, or boredom with the job. Ask about and plan for their career goals. Use this time to express appreciation for a job well-done, or provide a little course correction through feedback.

Fifth, Work on the Key Levers for Building an Effective Workplace

In the book First Break All the Rules, the Gallup Organization shared the results of a study involving 80,000 managers from different companies and industries. The study found that the best managers work consciously to create an effective workplace and that such workplaces have a set of 12 common characteristics regardless of the company's size or industry.

Authors Marcus Buckingham and Curt Coffman found that an effective workplace is one where employees can respond with "Yes" to the following 12 questions, quoted below in order of priority:

1) Do I know what is expected of me at work?

2) Do I have the materials and equipment I need to do my work right?

3) At work, do I have the opportunity to do what I do best every day?

4) In the last seven days, have I received recognition or praise for doing good work?

5) Does my supervisor or someone at work seem to care about me as a person?

6) Is there someone at work who encourages my development?

7) At work, do my opinions seem to count?

8) Does the mission/purpose of my company make me feel my job is important?

9) Are my co-workers committed to doing quality work?

10) Do I have a best friend at work?

11) In the last six months, has someone at work talked to me about my progress?

12) This last year, have I had the opportunity at work to learn and grow?

Your objective during your one-on-one meeting is to have a conversation that will help move three or more of the above questions closer to a resounding 'Yes' for your direct report. Be mindful of the mix of both short-term and long-term topics. It can be too easy to sacrifice the big picture when you're focused on the day-to-day.

Finally, End on a High Note

In The Collective Construction of Work Group Moods, authors Caroline Bartel and Richard Saavedra found that visible behavioral expressions within a group can directly affect the moods of its members. Consequently, people in meetings together can end up sharing the same mood in as little as two hours. Moods, as it turns out, can be highly contagious.

If you have scheduled your one-on-one meetings back-to-back and they all happen to be on a bad day, you must exert every effort to keep that negativity from bleeding into your meetings. If your one-on-one meetings end on a sour note, you and your direct reports will be leaving your meeting room with negative vibes that will infect everyone else before the day ends.

As the leader in your startup, you must set the tone for everyone on your team, and you have no better venue for positively influencing a direct report's outlook and mood than your regular one-on-one meetings. To the extent that circumstances allow, end the meetings on a positive note.

If your startup hasn't yet adopted the practice of holding one-on-one meetings, give it a try. Don't see it as a chore (oh no, another meeting!)--even though there will be days when it will feel like it. Instead, recognize that one-on-one meetings are a critical tool to create a more effective workplace, build a more motivated team, and strengthen the foundation of your company's future.

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