First (contracting) one-on-one

For the impatient, glance at the key takeouts at the bottom. “Listen” button at the top for vision free while hiking 😉

Like every first, it’s different, exciting, full of potential and makes you a bit anxious. “This time I am going to set them closer to where they wanna go. It’s going to be even better than the last one…”.

Knowing the rules of any “game” sets you better for success. Same goes for one-on-ones. Many things are different, company culture, leadership style, characters. Knowing which (collaborative) “game” you both are playing, what the limits are, and where the boosters lie, will enable you to play it better and rip the benefits stronger. Most of these limits and boosters are part of both of you. So what better way of discovery than a couple of questions to contract what you are going to be doing. Hence the craft’s name for it, “contracting”³ (or “partnering with your manager”² if you look at it unidimensionally).

Ease them into it. Explain it is a simple exercise of asking questions to both of you that will inspire conversation of what is expected of either.

The questions

The goals questions

Finding the motivations of people and the overlap with what the product/service/project/company wanna do, will reveal a way to push any of them forward. So one of them will not stay a contained effort, but rather, once overlaps are revealed, they will allow for the action of either to inert the other into progress. The interest in improving in how code is structured, for instance, may improve on maintainability, extensibility and in turn improve on being more efficient, and on delivery of the product. This might also reveal an organizational skill for the person, that can implicate benefit in improving on processes, Convey’s law for team organization, e.t.c. In turn, the product being in the payment industry domain, might fulfill the employee’s need to work within better standards, or the possibility to explore or push the boundary of an architecture. A traveling domain might better satisfy the person’s need to contribute to the human condition, more than working on a gambling domain, for instance.

1. What are your career long term (3–10years) and short term (3–6months) goals?
2. What are your private goals?

Make sure they understand its safe for them to be open and the answers are going to work to their advantage. Explain how. Give your own answers as well. They will also understand how they can help you fulfill your goals.

If you get too generic answers make sure you ask follow up questions. For instance:

a. What would be valuable for you in the one on one?
b. What, more specifically, are you excited about?
c. Why did you change your team, company?

The support questions

1. How can your manager support you?
2. How can your peers support you?
3. (for manager of managers) How can your team support you?
4. Which areas you want most support with?³

You should start practicing being silent even in your first one on one. Aim for up to 30% talking and rest of the time listening, and “resist the urge to suggest areas yourself if they are struggling to come up with them”³.

The feedback receiving way questions

Both of you want to understand how to fulfill as much of the feedback potential as possible. For that, you need to learn how it is most suitable for either to hear it. It’s one thing to master the skill of diplomatically relaying feedback. It’s even better when you know what makes the other less defensive. “Doing it in a way that you think they’ll be most able to hear it is invaluable”⁵.

1. How would you like to receive feedback?

If you need more specifics, drill down with some of the follow-up questions:

a. What medium do you like me to use (face-to-face, chat, email..)?
b. Routine? 1:1s or informal?
c. Transparent? Public or private?
d. “Do you prefer to get such feedback in writing so you have time to digest it, or are you comfortable with less formal verbal feedback?”¹

The limits questions

To me, these are the most interesting questions. Most are focused on what to do. But what not to do brings so much finesse to the one-on-ones. It reveals a big part of the mojo.

1. What can be a challenge for us working together?

Keep in mind, also, it is fine if they come up with preconceptions about you. This will change so the answers will change as well. Its important to start with something.

2. What makes you grumpy?¹
3. How would you manifest grumpiness (body, vocally…)?

If you know the signs of a negative feeling, you would be able to change the behavior. Grumpy is great since it encompasses a lot of emotions. Some follow-up questions if you need to drill down:

a. How do you react to a variety of negative emotions: disappointment, frustration, and anger?³
b. How do I know when you’re in a bad mood or annoyed?¹
c. Are there any manager behaviors that you know you hate?¹

4. What do we do when we notice that we are grumpy?

Make a plan on what to do so you get out of the situation. A good idea is to be able to be opened to each other and be able to share that when it happens.

The confidentiality questions

Some people want to be more visible to the bigger organization and some people wanna do their thing in private. Respecting this will help you move the person and product/company further.

1. How confident is the content from our meetings?³

This can be different for different parts of the organization. Think, their manager or peers.

Going the distance

1. How do you treat yourself?

Use this to accent a praise.

The resolution

To give a better chance to the contracting, think about posting them the questions before the meeting or placing them in the event. This will let them think about aspects they haven’t thought about before and provide a better quality for the first one-on-one.

“You started talking candidly, which should set the tone for further interactions.”³

You should also repeat this exercise in some time to reassess and be on top of things.

The testemonials

When leads asked how they felt about this formal format of contracting vs an informal approach, the following were some great insights in why contracting is valuable.

Although it might feel a bit more formal than usual, they love the grumpy question. They feel that nobody bothered to ask them and even they haven’t thought of that being a point of discussion, but when talked about, they felt it could be of big help.

They notice some aspects that they wouldn’t otherwise notice and explore.

The cadence announced by the first one on one felt like they are on a good path to find the right path to success on time instead of getting a late review at year’s end or quarterly.

Three key contracting questions and the revelation

1. What are your career and private long term and short term goals?
2. How would you like to receive feedback?
3. What makes you grumpy, how do I notice this and what do we do about it when we notice it?

The revelation: “Nobody bothered to ask me what makes me grumpy and I never thought it would be so interesting and important to explore to me.”

Summary of high level contracting questions

1. What are your career long term (3–10years) and short term (3–6months) goals?
2. What are your private goals?
3. How can your manager support you?
4. How can your peers support you?
5. (for manager of managers) How can your team support you?
6. Which areas you want most support with?³
7. How would you like to receive feedback?
8. What can be a challenge for us working together?
9. What makes you grumpy?¹
10. How would you manifest grumpiness (body, vocally…)?
11. What do we do when we notice that we are grumpy?
12. How confident is the content from our meetings?³

Resources

0. Coaching

General One on ones (for all seniority levels of managers):

1. Cadence (1–1s)
2. Agenda (1–1s)
3. First 1–1s
4. Prior to 1–1s (in the oven ..)
5. During One-on-ones
6. After 1–1s (in the oven ..)
7. Location (1–1s) (in the oven ..)

One-on-Ones for (Engineering) Manager of Managers:

8. Cadence (MoMs’ 1–1s) (in the oven ..)
9. With whom? (MoMs’ 1–1s) (in the oven ..)
10. Agenda (MoMs’ 1–1s) (in the oven ..)
11. During a 1–1 (MoMs’ 1–1s) (in the oven ..)
12. During Interviewing (MoMs’ 1–1s) (in the oven ..)
13. 1–1s with Senior Peers from other functions (MoMs’ 1–1s) (in the oven ..)

The “First One-on-Ones” Linkedin resource for additional audience to comment, interact and share with.

…

Reference

My experience. :)
[1] Camille Fournier, “The Manager’s path”, 2017, book
[2] Will Larson, “An Elegant Puzzle: Systems of Engineering Management”, 2019, book
[3] Dr. James Stanier, “Become an Effective Software Engineering Manager: How to Be the Leader Your Development Team Needs”, 2020, book
[4] Marcus F., https://lnkd.in/dghjKmQB, youtube videos
[5] Lara Hogan, https://lnkd.in/dnxKqMdh, blog