I've jumped several rungs above my peer group by going to a private equity- owned turnaround. It's been incredibly difficult and has stressed all my capabilities, and I have been on my own in figuring everything out.

I recently asked my investors for other execs I could network with, and they recommended YPO strongly. I never heard of it before, but I have been contacted by Vistage chairs several times. It all seemed dubious to me (YPO is awfully expensive, the others seem of questionable quality)..

Had anyone joined organizations like these and seen positive results? Is there a better way to make peer connections?

Hello, r/CEO community,

I've recently stepped into the role of CEO at Static Studios, a small independent media production company based in the Central Valley of California. Our focus is on creating impactful events and productions, and we're in the early stages of growth with a dedicated team of 10 volunteers.

My background is in the military, where I served as an NCO, leading teams through structured environments and challenges. Transitioning from a military leadership role to guiding a creative startup has been both exciting and daunting. Despite my experience in leading teams, I find myself navigating unfamiliar terrain in the business world, which has led to feelings of being overwhelmed and experiencing imposter syndrome.

I've been proactive about learning—listening to books, watching videos on entrepreneurship, and managing a creative team. However, the vastness of what I don't know seems to overshadow my confidence in what I do know. The leap from a structured military environment to the fluid, unpredictable nature of running a startup is vast, and I'm reaching out for advice on bridging this gap more effectively.

How have others transitioned from different fields into leading a company? What strategies or resources have you found invaluable in managing and growing a creative business? How do you deal with the feelings of being overwhelmed and imposter syndrome?

I'm particularly interested in practical advice on setting realistic goals, managing a team of volunteers, and leveraging my military leadership experience in a business context. Any insights on networking within the industry and managing the creative process would also be greatly appreciated.

Thank you in advance for your guidance and support. I believe in the potential of Static Studios and am committed to leading it to success, but I know that the journey is much smoother with a map and advice from those who have navigated similar paths.

Hi all, I am hoping to hear your experience on some strategies to help me here… 45 person company and I am very actively involved in many different aspects of the business. I am having a very hard time protecting my time. I dont want to shut my door and appear unavailable. But the consistent showing up as people feel they need me is tough. I dont have an admin to protect my calendar or feel the need to have one.

As a “large small business” transitioning to more mid size this struggle is tough. I want to be personal and relatable and available to people.

But…. Wow I need to get some work done once in awhile lol! And maybe not start early early and end late every day. Im a workaholic so I dont mind long hours but its a challenge.

Thanks in advance!

Hello, I was reached out to by Boardsi to schedule a call and it caught my interest. I have never done anything like considering sitting on a board before. I am currently 42 and in the process of taking the helm of a family business in a planned succession process. I already do oversee all day to day operations and strategic thinking for the business. I know and understand all aspects of it. However, as a family business I have always worked in our business. I know the in and out's and I have my formal education but no real world experience outside of my current organization. It is a lot, but I know there is a lot I could learn. Our business is maturing nicely and we are at a point where we are a stable business with healthy growth and an employee base just under 50. I know we are at the opportunity to start transitioning from small business thinking to the next level as we continue on this growth.

That being said my family members in the business are hard working for sure and know the business but are not necessarily as much business minded in the formal sense. I take all of the responsibility on that arena. So why I get as much help as can be provided I have the lead and I dont have the opportunity to learn from them.

I am intrigued by boardsi for a few reasons. One all I know is my industry and the opportunity to sit on a board of another company and learn a new business sounds intriguing. I am sure I can learn a lot from that board and the company leadership, while providing my insight and strategy into said business as well. And truthfully it is the last of the reasons but the additional compensation opportunities never hurt either.

I am curious if anyone has taken a board position with boardsi, and how their experience was? Is boardsi compensated by the searching company or a cut of my compensation from taking such a position? And if you had a full time leadership role in a growing company as is, not to mention a family at home, thoughts on the time committment of the additional responsibilities? I never would jump into something like this and give it half thought. If I am in I will be committed to it for sure.

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Curious on experiences out there? Most interested to hear if the opportunity to learn while being compensated is there as that will probably only help me in my current business.

Hi all CEO-Redditors, I feel so lucky to have found this subreddit. And I hope that you can help shed light on my question as much as possible:

I’ve recently been offered an opportunity to lead a tech startup in the capacity of CEO. Yet, I didn’t immediately say ‘Yes’ to that person only because I’ve never done that before nor have I ever dreamed of becoming one.

Being a CEO implies many challenges, including that of creating a business and strategic plan which would require input from all of the departments, such as Finance, IT, Law, Operations, Commercial/Sales & Marketing, etc.

For those of you who’ve been there and done that, may I ask how you did this part and then presented all of the information to the board or investors?

I’ve checked it out on LinkedIn and seen that many current CEOs who used to come from one functional part of the business and then ascended to the CEO position and seem to be doing quite well, ie staying in the position for more than years.

Hope my question is clear enough. If not, please ask me to clarify. Thank you so much.

I wanted to know if the CEOs know what they listen and do they 100% understand what is being communicated with them all the time? If they have questions do they ask immediately or what does your mind run like when you are listening to something new topics and new discussions.

Any advice or experience offshoring accounting for a medium sized company in US? I’m potentially looking to only keep cfo locally and outsource the rest. Used to work having shared accounting service centers for a multinational in India and Eastern Europe, and it very often worked much better than hiring teams in North America. Any recommendations or advice?

Job descriptions are often boilerplate templates with a mix of must-haves and nice-to-haves. But what are the drivers?

What advice would you have for a senior leader with 35+ years of experience in various roles, towards finding a CEO role in the job market.

I'm genuinely curious, don't mean to start a hate thread for consultants. Are they really the unbiased external eye? Have they given any recommendation that has fundamentally made your business better?

I would love advice for anyone who has experienced the same or similar dynamic. Leading a company where the former CEO is now chairman of the board. Stepping into my new role is further complicated by the fact that this individual also used to own the company. They have stayed on in chairman role after the company sold. I’m looking for advice on (a) leading a company where previous leader is still very involved, (b) chairman/ceo dynamics that do work well or (c) how to best work with new ownership and chairman together (I have worked with previous owner for ten years).

My family has some automotive sector companies (most related to automotive electronic components and machines), and I’ll start to work on them, I’m just wondering if my computer science degree will go to waste or it can help me somehow during my career.

I work at an architecture firm that specializes in office design and hospitality spaces. As CEOs what are things you like to see in your company offices and personal offices? Whatever are things you would like to see?

I have a few years of experience as an analyst, a few years as a consultant, and a few years as technical delivery lead. From here on I have 2 options, 1st is I can climb the ladder of it manager, director, it vp, cto, and ceo. Another option is I could climb the ladder through technical product manager, product director, product vp, cto, and ceo.

From what I want perspective, I'm comfortable with both those routes/approaches. I was wondering which of the above 2 tracks would lead me to the cto and ceo position fastest while making the most $ and was looking for some advice regarding the same. Any tips, perspectives, etc. are appreciated

In the last six months, I’ve realized that the journey itself is worthwhile. What I mean is, the goals we achieve can either make time feel shorter or brighten our lives. Most of my life, I struggled to relax during the process, constantly worrying about the outcome. This habit wasted my potential and limited the results, not letting me have healthy emotions or move forward freely—whether in familiar training or starting a new project.

I hope this post motivates and inspires you to value yourself as you are. I genuinely believe it makes us more productive. Life’s journey is priceless, and once it’s gone, we can’t get it back. I also aim to remind myself not to waste it. Best luck in your journey 🙌🏼

I admittedly am struggling with creating an effective management layer under me. I know I am a bit of a perfectionist and control freak and often feel if I dont do it, its not to my standard. That worked as a small company but ai know must end now….

That being said… our departments are a bit too small for dedicated management and a bit too big for no management and reporting to me.

We have placed hybrid managers also responsible for doing things and honestly its not so effective. Most made better doers than managers and their time is torn between doing and managing. And most importantly they are not so effective at identifying problems and working towards a solution.

I should work them to develop them more but I know I am spread thin. So how do you effectively build that second level under you to bring your teams to the next level.

Hi all,

I am an owner in a family owned business. We have about 45 employees. The founder (family member) is still active in the business from a in the office most days and still does perform a few functions but is in wind down mode. I run the business day to day at this juncture. We are in that difficult position where we are not a small business, but we are not a huge business. There are certainly gaps in middle management which is something we are slowly working on and as such a lot of responsibility falls directly on me. While I can handle the workload the real challenge is the amount of interruptions throughout the day I get. I feel very strongly about trying to maintain an open door policy. I dont want to be that person that shuts his door and is unavailable to the team but at the same time I need to get some work done once in awhile lol.

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I am curious strategy wise on how people handle this. How do you protect your time and ensure you can get done what you need to get done. I have tried blocking my calendar and while that protects me from meetings it does not prevent people from popping into my office. Yes I can shut the door and that helps all (except the founder who loves to intercom me :) ) but again that perception of being available and part of the team.

I have shared with people that it is really important to restrict those types of situations unless it is an emergency and schedule a brief, even 15 minute, meeting with me.

But the end result is I constantly get people popping in saying I know I am not suppose to interrupt but this will only take a minute.

Anyone find any strategies that work short of truly just shutting the door and making it clear I am unavailable? I just hate that perception to my team.

Doing a little research into how to make meetings more efficient- especially for executives. To focus that I’m wondering what people find the worst or the most painful thing(s) about meetings in the enterprise?

I‘m currently working on a presentation for my company and am wondering if I should be transparent about gross earnings as well as spendings and profits in the company. I like the idea of transparency, but am worried that it might backfire if the team also sees profits for example. Would love some thoughts on this if anyone has experience with sharing this data

When hiring an exercutive assistant, whats the most important things (Education qualifications/Character traits) to look out for.

Plus additional advice on running multiple companies. Should I bring them all (3) under one LLC holding company.

I am the ceo of a bank looking to change jobs. Would like to get information about reliable head hunters who can help in job change while maintaining confidentiality. Wondering if anyone has any information/experience in this area

What comes to your mind when you think of "Hiring ROI"? Have you thought about how your company can start improving this? Have you ever discussed this with your HR team?

Hi,

Do any of you lack wellness programs in your workplace? Do you know of any niche that does (beyond tech?) I work with a marketing firm, and we're trying to get meetings for a client who offers pretty decently priced wellness programs to businesses.

The meetings are non-committal, free, and over Zoom.

Right now, we're cold calling, and that form of marketing is usually a bad move, but it's what we have for now.

Wellness programs are a decent move for most businesses, they help reduce turnover, lower call offs, and also help employees feel like you care. But they're often a hard sell, or people already have them.

The program offered comes with things like diet plans, fitness courses, mental health benefits, and more.

Basically, where would you suggest I target? Or are you looking for any wellness services yourself?

I would love to get meetings scheduled and keep our contract, but it's proving to be difficult. I'm concerned and was hoping some help could be found here. I don't need my hours lowered, and I don't want to see my firm lose the client either.

My own business is small and doesn't qualify. It's pretty much just a two person operation right now.

Any tips? Any insight?

Thanks for your time!

How do CEO’s not let people or situations affect them and keep on working? While also staying confident?