How bosses can make it easier for employees to manage up

Onward and upward.
Onward and upward.
Image: Reuters/Thomas Peter
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In the last year, our team at Uncharted has tripled in size. But the metrics of staff growth matter less to us than the metrics of how our new staff become fully integrated team members contributing to our mission. The growth in headcount has challenged us to re-examine how we onboard people and how we manage our one-on-one relationships. It’s made us ask the following questions:

  •      How might we accelerate the building of trust between two people?
  •      How might new hires more quickly feel permission to fully contribute?
  •      How might we provide a roadmap for thriving interpersonal relationships, for regular and honest feedback, for courageous (and hard) conversations?

Personality tests are intended to answer these questions, but my experience with personality tests has been that they are far more interesting than useful. So I set out to create “The User Guide to Working with Banks,” a practical guide designed to accelerate the time it takes to build healthy, effective relationships with my co-workers. Since I’ve created mine, members of our team (new and existing) have begun to create their own, and we’re building a shared language and a set of permissions and guidelines to work in ways that bring out the best in us.

User manuals like these work best when there’s one for everyone. But there’s a particular power in a boss creating a roadmap that helps their direct reports manage up. It creates permission for people to show up, communicate, and work in ways that lead to more trusting work relationships and better long-term outcomes, and helps people avoid unproductive feelings like being intimidated by a boss because of a title. I could go on about this, but instead I’ll just share my own guide (which is available to my own team in a shared document and includes comments from some of my colleagues who know me best) in the hopes that it inspires you to create one, too.


The user guide to working with Banks

Why this guide? The purpose of this guide is to accelerate the time it takes to work successfully together. I’ve attempted to make this a roadmap to an optimal working relationship by sharing expectations, offering insights into my working style, and spelling out practical how-tos for working with me. This guide doesn’t intend to tell my story or provide background on who I am; there is far more to me and my lived experience than what’s in this guide, so consider this simply a start. There is no substitute for face-to-face time together.

Who is it for? The people I work with—both inside and outside Uncharted.

What was the inspiration for this guide? I can’t take any credit for this; I got the idea for a user guide from this article.

Communication Norms

Over-communication: I prefer over-communication to under-communication. I have the capacity to digest a lot of information, so please don’t think you’re burdening me with status updates and questions. Do not assume that I am too busy or don’t want to hear about your progress.

Cydney comment: Make sure to frame what you want Banks to do with the information you share with him: an action he needs to take, something for him to keep in mind, etc.

How to communicate with me:

Text message: For anything urgent. This is the fastest way to reach me

Phone call: I don’t usually answer my phone and am terrible at checking my voicemail.

Slack: For quick questions, updates, or brief conversations during working hours. I might not respond to Slack right away, however.

Email: I read all my emails, but don’t respond to them all. You can reach me this way too, especially for longer-form questions not suitable over Slack or text.

If you are assigning me a task or requesting that I do a thing or attend a meeting, please assign it to me in Asana and include Cydney.

My phone has no notifications for emails and slack.

Problems versus solutions: I am not one of those people who “doesn’t want to hear about problems, only solutions!” You should feel permission to bring problems to me that we can troubleshoot and co-explore.

Sophisticated language: I really dislike sophisticated, complex, abstract language. I’m not that intellectually quick, and I have to work extra hard to pay attention and convert that language into something understandable. Fewer more concrete words are better.


You lead our one-on-ones: I expect you to run the one-on-one meetings that we have (either our weekly meeting or one-off meetings around key topics). This means:

24 hours before the meeting you send me the following:

Success for the meeting: what your desired outcome is

My role in that meeting: Am I helping you troubleshoot an issue? Am I making a decision? Do you want to just chat and feel heard?

Agenda for the meeting

Any pre-work I can be doing ahead of time (optional)

We can co-create a structure for these meetings together.


Normalize feedback: Feedback is terrifying when it’s done rarely and not a big deal when it’s done constantly. I prefer to give and receive it often.

I expect feedback from you: Feedback should be bi-directional for a healthy working relationship. If I’m not getting feedback from you, I’ll think something is up.

I respond well to feedback. So don’t be afraid to speak directly.

I expect you to tell me how you want me to give you feedback: You know yourself better than I do, so you need to give me a roadmap for how best to provide feedback to you. Don’t expect that I know.

Take responsibility for your experience: I’m not a mind reader, and I don’t want to be guessing about what I can do to make you more successful and happier: If you are unhappy, upset with me, stuck because of something I am doing, not feeling clear, or anything that isn’t working for you, I need you to tell me. Nothing will get better if we don’t talk about it.

Feedback is positive too. If you do a great thing, I will tell you. If I do a great thing, you should tell me.

My pace, energy, and working style

Fast pace: I run at a pretty fast pace and stack my day with meetings back-to-back. It works for me, but I know that it doesn’t work for everyone. I don’t expect you to conform to my working style and pace. Also, don’t confuse my busy-ness for inaccessibility. If you need me for something urgent, I can shift things around.

Intense/focused energy: It’s been reflected back to me that I can give off very intense/focused energy when I’m working. If you are picking up intense/focused energy from me, don’t think it needs to be matched. Let me know if my energy is making you anxious/stressed.

Stress and impatience: When I am stressed or feeling the need to move quickly, I will fall into impatience with the people around me. I’m working on this, but you have permission to call me out if you’re sensing I’m giving off impatient vibes.

Personality and quirks

Sharing external updates: I have an external role, and there are times when I’ll come into a one-on-one meeting with you and want to share high/lows from a solo external meeting. I don’t need you to do anything with what I share; I simply find it helpful to reflect a solo external experience with someone who gets it (or some of it). No action for you here, just a heads up that this will happen.

I use a lot of metaphors: I find myself using metaphors quite a bit. The team has pointed this out, so I’m trying to use more direct language. Please let me know if you find yourself confused.

Hard on myself + high standards: I have high standards for myself and am often hard on myself. I am working on acknowledging things I am proud of and practicing more self-forgiveness when I mess up.

People pleaser: I am a people pleaser, and I want you and others to like me. No action for you here, just a heads up.

Cursing: I curse decently often. It’s mostly about situations, not people. Let me know if this uncomfortable for you.

Asking for help / being the hero: I am prone to adding more tasks onto my shoulders instead of being thoughtful about how I ask for help. Sometimes a “hero-complex” arises because I want to protect the rest of the team from a heavy workload. I invite you to call me out if you notice this.

Overwhelming and random ideas: I’ve been known to come out of a meeting with a new/crazy/big idea and want to share it with someone. This can be distracting, overwhelming, and/or confusing for how it fits into our existing strategy. I try not to drop these “idea bombs” on the team, but it happens. When it does, please clarify with me what I want you to do with that information, and that will help me set better context.

I like to externally process: I am an introvert, but I am an external processor for things that 1) I am excited about, and/or 2) feel unresolved in my mind. This means that I sometimes talk a lot. You should feel permission to do the following:

Interrupt me and tell me that this is not the time for external processing

Clarify that I am, in fact, externally processing and then meet me there

Personal stuff: I won’t share much about my personal life unless you ask me, which you are welcome to. It’s not off limits. I’m just not good at volunteering it.


Slow at decision-making: I am not a quick-on-my-feet thinker, so please give me time to process (especially big) decisions. If you need a decision on something, give me enough heads-up so I can start to process it.

Cydney comment: “Once he does make a decision, though, Banks is very fast to implement it. This can feel a little like going from 0 to 60, so just heads up that if Banks mulls something over and then agrees to it, the change starts the moment he says yes.”

I don’t like being put on the spot: I might give you some quick thoughts and then return later with more refined thinking. Giving me time to process will lead to a better decision or response.

Ash comment: When you bring something to Banks’ attention, that something will receive its fair share of thought and consideration—and then some. Don’t be surprised if a small comment on your part results in a larger conversation two weeks later after he has had his internal deep dive. He listens to and cares about everything you say.

Holding a CEO title

Being a CEO doesn’t mean I have all the answers. If you come to me looking for answers, I will disappoint you. I’m better at co-exploring a question together to arrive at the right answer with you (or so you are equipped to arrive at the answer yourself). Being the CEO doesn’t mean that I am right, so you should press into the data I am using to form my decisions and perspectives.

Being a CEO means that I am further away from the issues/impact/people than you are. This means you need to weigh my input alongside your own experience. I might be out-of-touch.

I am not the smartest person on the team. I have no idea who is, but it’s not me (I can send you my academic probation letters from college as proof). So don’t take my advice/counsel as gospel.

I started out as an unpaid intern on this team. And I’ve served in a number of roles within the organization before my current role.

What triggers/frustrates me/erodes my trust in you:

Making excuses instead of taking ownership

Saving face and protecting oneself, instead of owning mistakes

Making emotional, irrational decisions

Not being visible/transparent in progress, challenges, and questions. Being silent makes me question how engaged you are in the work (whether this is true or not)

How to earn my trust

You over-communicate with me

You seek understanding

You challenge me from a place of understanding (instead of challenging me before you have sought understanding)

You acknowledge what you don’t know and how you are learning

Professional development

Your professional development is your responsibility. I can help facilitate your own professional growth with introductions to mentors, access to opportunities, direct coaching, etc. But it is up to you to lead this process for yourself. Don’t expect me to magically understand how you want to grow. You need to tell me what you need, and I’ll do everything I can to support you.


Hours: I don’t expect you to work on nights or weekends, and you shouldn’t expect me to work on nights or weekends either. Sometimes work requires a bit more here and bit less there. Take responsibility for your hours and how work is situated into your life.

After-hours communication: From time to time, you might see an email from me after hours on nights or weekends. I know there is this thing where if someone sees an email from the boss, they feel compelled to respond right away and show they’re available. This is dumb. Don’t respond until you’re back at work during normal hours.

Be punctual: I don’t like people being late.

Lunches: I don’t really take lunches during the day, but you should feel full permission to take a lunch break.

Ash’s comment: We need to work on this.

Pronouns: He/him/his