What?
These are one-on-one meetings that you have with each of your direct reports on a regular basis.
Why?
These are not status updates - not about the work. They are more important (and less urgent) than that. The point is to listen and learn. Learn what your employee thinks, what their goals are (career and otherwise) and what they see from customers and others that you do not.
It's also a time for you to help them with professional development. Meaning help them to improve their ability and advance in their career. This means you should know their career goals. Often in a small company, you don't have an adequate career path for everyone. So if they're going to move on, wouldn't you like to know about before they give their 2 weeks notice? Also, some people don't really have career goals. But they do want to make more money. You can use this time to show how they can become more valuable to your firm.
When most people leave a job, it's because of their immediate boss. This is the chance for you not to be that kind of boss. It's a time for you to show that you care about them as a person, about their progress and professional development, and about their perspective and opinions.
The relationships you build by doing regular 1:1 meetings engenders loyalty from your team and gives you insight to help you do a better job. After all, as a manager, you get results through others.
How?
Schedule them regularly in advance. Don't Reschedule!
A regular schedule is critical so people don't feel like they're being called down to the principal's office. If you do nothing else but manage people, you could meet with each of your direct reports once a week. This is most useful in fast moving industries where people don't stay in the same job for very long.
If you do some other work besides management, weekly meetings with everyone may be too much. Still book time in your schedule every week, then rotate your people through. So you might meet with each person every two to six weeks.
Book 45-60 minutes. Plan to do the meetings in 45 minutes or less and use that extra time to prepare or regroup your notes. If it feels like you're finished in 20 minutes then you probably need to build up more trust so they feel comfortable talking more. Stick with it.
Spend Most of the Time Listening
This is their meeting not yours. Have them prepare what they want to talk about. You may have to prime the pump with some questions (see below).
If you (and they) are new to this it will take a few cycles to develop trust and get real. Keep at it.
Be vulnerable. This is not a time to lecture - it's a time for you to learn. Talk about mistakes you've made. If people bring up your short comings, don't defend. Say thanks.
If people make suggestions, take note of that. You don't have to agree or implement everything they say, but take the input seriously and get back to them about your decision and reasons.
Take notes so you don't go too long without talking about certain topics - and don't bring them up too frequently. Date each page of notes. Especially note the positives. Those are easy to forget to mention.
Prepare
Before each meeting, review your notes and think about a few questions you want to ask if the conversation lags. After each meeting jot down your thoughts and what you might want to cover in the future.
What to Say
This is not about the status of their normal work. That should be communicated in other ways at other times.
You can open with "What's going on?" or something general to get a sense of their emotional state and give them a wide opening to share what's on their mind. But if you have an agenda, share it early (you don't want them to feel blindsided) - and then get their input on what they want to discuss. Their agenda usually takes precedent.
Here are some questions you can have "in the bank" that you can pull out in your prep time. Note some of these will not get a good response until you've built up some trust. (Many of these come from Mathilde Collin at Frontapp.com and Clair Lew from KnowYourTeam.com)
- Am I giving you enough information to do your job well?
- What are you hearing that I need to know about? [Don't ask them to rat on employees but if they work with customers you need to know what they're hearing.]
- What are your career goals or retirement goals?
- What do you think is the most overlooked area of the business?
- In the past month, what have you been happy about? Less happy about?
- Any questions for me? Feedback for me?
- Where do you think we're behind that other companies are excelling at?
- Share something you think you can be doing to help then ask "What do you think?"
- What can I do to make your professional life better?
- What’s the biggest problem of our organization?
- What don’t you like about our product?
- What would you like to achieve by the end of the year?
- What would you like to learn?
- What's most frustrating about how X is going so far?
- What's most surprising about X,Y,Z?
- What would you like to be better at / in which areas would you like to grow?
- After X+ month/years at this company, how do you feel overall?
- If you were me, what would you do differently?
- What are the things you’ve done since you joined the company you’re the most proud about?
- Is there anything I could do to invest more in your growth?
- What’s the split of your time today between X/Y/Z? What would you like to spend more/less time on?
- Do you think I’ve been a little micromanaging with how I’ve been following up on projects?
- Have I been putting too much on your plate and do you need some breathing room?
- Am I giving you enough information to do your job well?
- Could I be doing a better job outlining the vision and direction for where we’re headed?
- Have I not been as cognizant of reasonable timelines, like I should have?
- Am I interrupting you too much during the day with meetings and requests?
These meetings can sometimes be a the time for those (infrequent) hard conversations about putting the vision into practice, making tough calls, etc. But if that's all they are, either you have the wrong person in the job, or you haven't shown them adequately that you care about them.
One on ones can also be a time of training, coaching, or professional development.
