What do I talk about with the CEO?

January 11, 2021 6:39 AM

I work for a company of around 70 people. The CEO has mentioned that he'd like to have one-on-one meetings with employees beyond his direct reports. The CEO has told me directly he thinks it'd be good if he and I did this. My manager has said, independently, that she thinks it'd be good if the CEO and I did this. I don't have anything to talk about right now, how do I do this?

The CEO is very accessible so it's not a problem for me to go to him if there's some feedback I want to give or if I want to get his input on something. But there's value in having regularly scheduled meetings, and I want to learn how to check in with him every few weeks. I guess my personality is such that I don't go to people above me unless there's a specific concern to talk through, so I'm struggling to wrap my mind around what actionable things to talk about.

A few other details:

• We're a software development company, and I'm one of maybe three employees who has been on the customer side of things in our industry.
• I'm a senior technical employee, and one of a handful who has experience working for other development companies.
• We tend to bring in new employees as interns and train them up through the ranks, which is great, but it also means that I feel like we're missing a lot of "real-world" and industry experience. At times it seems that we're reinventing too many wheels that are solved problems in the greater software dev world.
• The bulk of development happens in a different office than mine, so while I probably have experience to help improve inefficiencies that come up, I usually only hear about big picture problems in team meetings.
• I have 1-2 internal project meetings a week that the CEO sits in, so I feel like I have a decent amount of face time with him already

Maybe this is a simple question. But how do I have regular one-on-one meetings like this when I don't have a clear direction in mind for what I'd be talking about?

posted by Nonsteroidal Anti-Inflammatory Drug to Work & Money (12 answers total)

I am not in industry, but if both the CEO and your manager are saying that it would be a good idea for you to talk to the CEO, that maybe sounds like they have something in mind that they want to talk to you about? Which, given the context, sounds perhaps more like career advancement opportunities than anything negative? The CEO almost certainly has an agenda or general set of questions to ask people for these general meeting with everyone meetings, as well. (If not - if your CEO is just doing this rather unusual thing for no reason or aren't, themselves, clear on why they are doing it, that's not great business leadership.)

In general, asking questions to better understand the business, specifically in directions that would make sense for both your current role in the company and potential promotions or new roles, is likely a good topic to talk to the CEO about.

Given your concern about not wanting to undermine your direct supervisor by skipping over them in the chain of authority, you could also simply ask them for more information about these meetings are about and ask what they suggest?
posted by eviemath at 6:49 AM on January 11, 2021 [6 favorites]

I mean, your details list could very easily be an agenda!

• Our employee pool does not have a lot of customer-side experience in our industry. Is that presenting any challenges or opportunities?
• We also have only a handful of employees with experience working for other software development companies. Is that presenting any challenges or opportunities?
• For instance, one challenge I've identified is that the lack of hiring folks with real-world and other experiences leads to us needing to invent solutions that might already have been done, and done more efficiently, elsewhere.
• I'm only hearing about big-picture problems in team meetings, but I think with my experience I could be helping improve inefficiencies that come up in the development office. How can we make sure my skills and knowledge are being best used?
• Are you seeing any trends across my project meetings that you sit in? Is there anything you want to discuss that is more appropriate one-on-one than in those larger forums?

Also, since you are clearly already thinking about the case for diversity of experience in new hires, that would be a great time to also talk about diversity of identities in new hires. There's definitely a business case for that.
posted by solotoro at 6:57 AM on January 11, 2021 [13 favorites]

I would use the list of observations you've made here to prepare, but assume that the CEO will steer the meeting. If he wants to meet with people, it's because he wants to get some kind of insight. If it's about the employee pool, the development process, the office culture, etc. he'll ask.

So your best bet is to prepare your thoughts on these subjects and see what he says. Make sure you're thinking of the strengths and the weaknesses of the company in all these aspects, as well, because if he asks a question and you have suggestions, it's still going to be good to phrase it as "we do X very well but I think we could be stronger in Y" rather than just "we should be doing Y."

In your preparation think especially about the areas you have experience in that others don't; if they've chosen you to talk to, it might be specifically because you have seen how other companies do things and you have seen how customers feel about things.

Also, if this plan gets to the point of a meeting being scheduled, it should be okay to ask for an agenda, even a general "what kinds of topics would you like to discuss," ahead of time so you can come prepared.
posted by gideonfrog at 7:03 AM on January 11, 2021 [5 favorites]

couple ways to frame this but first be honest with yourself about your career aspirations. do you want to promote up to executive level someday or do you want to stay technical to some extent? thats really important. since this is meant to be a routine thing (if i read that right) you do not have to accomplish everything in one meeting. i would start the first meeting following and listening for prompts but if asked i would outline something like using these meetings to take the opportunity to report:

1. systemically what is working (postive)
2. systemically what isn't (negative with solutions or commentary)
3. who on your or adjacent teams has been killing it and specifically why that matters
4. small things (tools, people, effort, vendors) that were a boon to a recent small setback
5. same as 4 but in the negative (focus on NOT people for this one, more things, tools, concrete things an executive can wipe away with dollars or human capital)

basically if you went in and the CEO was like "it's your agenda and this is a vacuum you must fill for 60 minutes every 2 weeks" you could do well for the company, your good peers, and yourself with the above frame work. you are giving thoughtful incites at both micro and macro level. this lets senior executives think strategically (1, 2, 3) as well as being responsive and empowering you by doing things to support more micro level issues (4, 5).

additionally, if this becomes routine, talking about "agenda" items from the previous meeting and if they had a positive or negative impact honestly, or if they had the intended or any unintended consequences will both provide a framework for this being valuable time spent in routine long-term. it also allows instantaneous feedback on both how your executive is doing and how good your feedback is.

take this as a good opportunity to uplift you, your peers, and your company; and a good way to evaluate the long term prospects of success by reading your company's senior executive staff's performance.
posted by chasles at 7:08 AM on January 11, 2021 [2 favorites]

I have meetings monthly with my CEO (company size about 3x yours) and am not a direct report of theirs. In our meetings, they rarely, if ever, bring topics to talk about. They are, though, someone who LOVES details and hearing about new activities, etc.

As a result, I always bring a couple interesting examples of ongoing work to talk about. In some cases I'll have a direct question to ask of them: what do you think about this approach? what would you add to this list? or I'll have a direct request: I need some support on project X that is your initiative, as I am feeling overwhelmed, would that be possible?

YMMV, and I second the advice upthread to see if you can get some more guidance from your boss and/or the CEO. I would, though, be sure not to waste a single second of time that you have in front of the CEO, and have something to show off, get feedback on, etc. ready to go if the meeting happens to be running out of steam or ending early.
posted by chiefthe at 7:12 AM on January 11, 2021 [1 favorite]

Can you send an email that says this:

"Hey, CEO. Hey, Manager! Thanks for suggesting this meeting. I'm curious: Is there anything I need to to to prepare? Am I expected to show up with topics to talk about, or do you have some topics in mind?"
posted by ManInSuit at 7:41 AM on January 11, 2021 [1 favorite]

If he hasn't shared an agenda, then there isn't one. But you can still tell how it will go.

You don't know this guy, so the first thing that will happen is your introduction. Hi, I'm NSAID, I've been here for n years. Before, I used to work at $other_place - then I came here as $first_role, and switched over into $current_role in $year. First two minutes are now over. You survived!

But, he doesn't know what you've been working on. So then he'll say: ok cool, what have you been working on lately? And you'll say: mainly $project1, but I'm also involved in $project2

Then he'll say: oh, I heard that $project2 has been quite difficult, what's your experience been? And you'll say: well, we did $first_thing really well, but then $second_thing happened and it caused $problem, so we had to make $fixes and then...

And at that point you're just having a normal work conversation, albeit slightly weirded up because of the power differential, which you should do your best to ignore. Just lift it up a bit from the lower-level details & show the bigger picture, so the guy doesn't get bored.

There's no need to be all jazz-hands about how awesome you are. He's asked to see you, so you can assume he already knows. If it turns into a regular meeting, you'll already know what it's like & what the guy expects you to bring.
posted by rd45 at 9:18 AM on January 11, 2021 [1 favorite]

I watched the owner of a similarly small company do this, not one-on-one but in small groups. In his day job he was a billionaire bank president, this was just a small company he had invested in on the side. The meetings were enormously beneficial for both sides — employees got to understand him and his priorities; he got to understand where there were strengths or problems. That's what your CEO is looking for. I would not worry too much or try to prepare to0 much. Have handy a short checklist of what you've been up to, if you want, but the CEO will take the lead in directing the conversation. Just be yourself and be honest.
posted by beagle at 9:43 AM on January 11, 2021 [1 favorite]

It's never bad to ring attention to a colleague or process that is good and deserving of praise.

It can be trickier to discuss things that need improvement, without sounding like a downer.

If it's as open-ended as you indicate, then expect a little small talk followed by a prompt (question) by the CEO. Feel free to bring along your notes, above, on a sheet of paper, as well as the names of one or two people/teams that you want to advocate for. :7)

If it was bad news or an assignment, they just would have scheduled the time and made you appear, you know?
posted by wenestvedt at 10:13 AM on January 11, 2021

I would also recommend that you utilize the opportunity to think about what are the strategic issues that are facing the company and how you can help address them (without appearing to be scheming). At this level, the vision and thinking is at a very strategic level. If you already have thoughts and ideas about where the company is going this might be an opportunity to confirm them, gain traction on initiatives, etc... It doesn't hurt to show that you've got the interests of the company at heart as well.
posted by kookywon at 1:42 PM on January 11, 2021 [2 favorites]

But how do I have regular one-on-one meetings like this when I don't have a clear direction in mind for what I'd be talking about?

If you assume 6 people per manager, you're looking at like 60 staff, 10 managers and 1 CEO gets you to 70. So basically this is a skip level meeting. A highly renowned management consultant team doesn't recommend this practice, but here we are. This feels like a prelude to a promotion to management, IMO.

The general concept of a 1:1 is to build the relationship, build trust. And by scheduling 1:1s and keeping them, you have a built-in point to communicate and keep interrupts low.

But how do I have regular one-on-one meetings like this when I don't have a clear direction in mind for what I'd be talking about?

Ask questions. 1:1s don't need to be dog and pony shows. If you have the time, learn how the person ticks. What are their hobbies, how old are their kids, if any. Do they enjoy gritty details, or are they more interested in beating the competition than how, etc.

Like I mentioned before, one minor gain of 1:1 meetings is a planned checkin point that can replace the ad-hoc Q&A sessions you have now. So I'd start there; whenever you're thinking of asking a question in the moment, see if you can proceed without an answer, write down the question in your notebook and ask during the 1:1.

And I would advise you not use the time to persuade the CEO to overrule your boss, if the possibility arises. Or discuss proposals your boss hasn't seen. At least not without her informed consent. The last thing you want is to damage your relationship with your boss by excluding them from the conversation, or making them look bad in front of their boss.
posted by pwnguin at 2:10 PM on January 11, 2021

I've done something similar from the manager perspective (meeting with people who are managed by people I manage). The main aims have been:

(1) To understand what good practices are being done by people who are working "on the ground", with the aim of either disseminating these more widely, or making connections between these people and other people who are in similar situations elsewhere in the organisation. These often don't get to me by the usual "chain of command" because they get abstracted away by the intermediate manager who is concerned with summarising, addressing KPis/targets, and focusing on problems rather than innovations.

(2) To understand what parts of the infrastructure and working practices are getting in the way of people doing their jobs. Where are the inefficiencies, information gaps, and shadow systems that get in the way of efficient working? Often these are not noticed by the intermediate managers who just think that a particular team member is just "making a fuss" about something; but when you talk to lots of people in different teams, you realise that there are some problematic systems/practices across the organisation.

Overall, to me this is about "grain" - its about understanding those things that are important "on the ground", but which get lost through summary/abstraction in the usual reporting process.
posted by Jabberwocky at 2:51 AM on January 12, 2021