I have talked with many CIO's who have gone through similar transitions in their own career. Starting as very technical and needing to transition to managing people, corporate functions and major projects. These transitions and letting go of personally being the smartest technical person in the room is often difficult. You move from your comfort zone of being very competent into a "newbie" role trying to figure it all out.

Each company is different. Your description makes it sound as though your company hasn't really thought it through very well - "just give him resources and he will figure it out". Sometimes this kind of sink or swim approach works but it could clearly end badly for you and the company.

You are no good to the company if you seriously burn out and crash. It feels like you need to push harder on the getting training and help. And, make sure your headcount lets you hire somebody in a support role that can hopefully take care of a lot of the little details of running your department.

It is a conversation with your VP at this point. If I don't get the help you have told me I can go get this is going to sink, its going to be my number one priority.

The other thing you need to find is a mentor, if you don't have any one in your circle (a former boss works, someone else who has been promoted) then you need to find outside help. Start looking for life coaches and or professional coaches, you may need to go through a few of them, but you might find someone you like and who can genuinely help you out.

Don't just shanghai someone because he came through the office door. Hire someone with a clear goal and determination in your mind, something like "You analyze, refine, visualize and optimize workflows in this team" or "You're the guy to run around, collect business requirements, identify stakeholders, and priorize tasks with them".

And once they are in the team, throw as much of that responsibility in their direction and let them handle it. Control and support them as necesary. For one, this is the only way to reduce the workload on yourself. However, I've also found this to be a great motivation - people like having a purpose, a goal and feeling needed.

Since you are directly reporting to someone who would otherwise be your skip level manager, you will need to fill in for your manager and ask for the correct job title to begin with. This will ensure two things:

1. Your responsibilities will be algined with your title; and

2. You will have better access to information and authority you need to build the right team, in addition to doing the right thing for people who already report into you.

I've been thinking of pulling together a mastermind of other programmers-turned-executive so we can talk about these problems together. I'm seriously peter principally-ing over here. ;)

Anybody interested?

Me:

Mid 30s Director of Technology Team of 10 + part timers. No College. Two failed saas products.

Email address in profile.

Next don't do it all yourself--it's suicide. Delegate those responsibility groups one at a time as you catch that new owner up to speed. If you don't know yourself, then point/pair them with someone who does.

Once everything is delegated your new job is helping those new managers succeed and focusing on the things where you uniquely bring value.

You can do this, just take it a step at a time. It only feels insurmountable looking at it all at once, it's an illusion.

If you keep saying yes (to everything you did before) and yes (to everything you are discovering you can do), it is only human nature for individual requests to increase to the point where they collectively overwhelm you. You could individually re-negotiate boundaries and committments, but that itself is work and requires political skills. A public change in title and a financial change in compensation will require executive approval and that process will help change company-wide perception of what tasks are the best use of your time.

Once that is out of the way (increasing your price as a form of demand/flow control), find good books and external mentors on:

  Leadership (managing down _and_ up) [1]
  Project Management (execution logistics) [2][3]
  Communication & Politics & Sales (human semantics)

[2] How to run successful projects (3rd Ed), http://www.amazon.com/How-Run-Successful-Projects-III/dp/020...

[3] Adaptive Software Development, http://www.amazon.com/Adaptive-Software-Development-Collabor...

http://www.audible.com/pd/Business/The-Advantage-Audiobook/B...

The Manager Tools podcasts have a lot of very useful advice that I think would help you. I recommend subscribing to their "Basics" feed to get started, and then listen to the full feed. http://www.manager-tools.com/podcasts/basics-rss.xml

You can see their whole "map of the podcast" here: https://www.manager-tools.com/map-universe/trinity-one-ones. It's overwhelming at first because they have almost 1000 casts. But you can navigate through the list to find the topic you're struggling with, and download the podcasts from there.

I can tell you by far the most material impact on my ability to take on more responsibility has been having a great manager (not just a mentor). A manager knows what work you're being asked to do, sees you try to do that work, and can give you feedback on the work that you're doing. A mentor just does not have that context.

It's so important that one of the questions I ask when interviewing people (at any level) is tell me about a great manager you've had. And a shockingly large number of people (even directors or VPs with impressive resumes) will say "I never had one, but I wish I did."

This is a longer-term advice, but I would make it a career goal if you want to grow to try to find a really great manager.

I reported directly to the CEO. I coped with this as long as I could fighting through burn out until I finally let him know we needed to expand the team. I was buckling under all the tasks. I spelled out clearly how it was far too much for any one person to handle.

We've slowly over time expanded the team until we now have 5 developers, which is still less bandwidth than we want but it makes things a lot more manageable, because we now as an organization accept a more realistic view of what we can do with the team we have.

I would say try talking to your manager about the reality of your situation. Have a real conversation about your concerns. If they go unheard or nothing comes of it, then it's probably time to move on.

Now would be a good time to assess your manager's history and learn to delegate the things you may have been doing on your own to others like they did. Your manager should be able to help you do this.

If this is an established company then this can't be the first time they've been in this situation, so there's probably a misunderstanding somewhere.

If this is a new company then it could be that they are learning this process as well.

If you haven't actually been promoted or your manager can't or won't help you grow into your new position and work through these issues then something's wrong. Beware.

1. It's really hard to do.

2. Few people have themselves been trained on management.

3. Faced with 1 and 2, people focus on their own, more familiar personal deliverables.

Therefore, if you want things to change, you'll probably have to make some specific suggestions. And to do that, you should do some homework. I highly recommend starting with Managing Humans by Michael Lopp (http://www.amazon.com/Managing-Humans-Humorous-Software-Engi...) or maybe The Hard Thing About Hard Things by Ben Horowitz (http://www.amazon.com/Hard-Thing-About-Things-Building/dp/00...). Spend an hour or two with each book and you'll have a better idea what can be done, and why.

What you're finding is that working as both a full-time manager and full-time engineer is very difficult, borderline impossible. Eventually, you'll have to choose. An increasing number of small companies are starting to understand this reality, and allow their top people to grow into either technical leadership or management leadership roles. Expecting both, simultaneously, is not realistic.

Where your responsibilities start to stretch to, say, handling conflict between stakeholders, other stakeholders, and non-stakeholders, I suspect that you will either thrive on that sort of situation - and connive ways to benefit from it - or you will always hate it, and I'm not sure any amount of support or training will really help here.

Lastly, if you are doing HR-type duties, then you really do need training here. Sometimes common sense really does not apply here, only prior experience, and you should not be expected to handle these types of tasks without proper assistance and guidance from people qualified to do that.

It was great to have my name on lots of projects, but after a while, it becomes impossible to manage it all.

Read or listen to the 4 Hour Work Week, its really about 10X your productivity.

Don't let your lack of degree or business training discourage you. A lot of leaders at start-ups today have similar backgrounds, and are learning on the fly. One area I found difficulty assessing was identify which stress was me growing into a role versus which stress was self-imposed. I worked with an executive coach to help learn the difference and make some small tweaks to my behavior.

Hang in there, say no more often, and reach out to others who have gone through a similar transition for help.

Do exercise coupled with controlled breathing, specifically with prolonged exhales, which tells our nervous system that there is no fight here. Do a tiny walk outside every two hours of coding, and consider yoga. Personally I also signed up for Blue Apron or similar mailed recipe kits because I found those instructions to be a relaxing level of activity, better than TV but still winding down, and there are those healthy diet benefits. I also rigged a sit / stand workstation with email on the low monitor and code on the high ones so switching position just happens.

It's very important that you allocate some time to each area - upto 2 hr blocks of time for coding and architecture, 20 minutes for management tasks and a block of time for firefighting/reacting.

Also schedule in time for exercise, sleep, and just general downtime. All of which are very important.

Lastly, drop anything that's not important and delegate whatever you can. From your description it looks like you will be getting new hires to help you out soon. Just ride it out until you get support and make sure you don't burn out along the way. All the best!

e.g. Sick leave - grab a warm body & tell them they're in charge of sick leave now.

If you're reporting to the VP then you are reasonably high up the foodchain and thus you are (or should be) entitled to make calls like that.

Hopefully your VP can serve as an internal mentor and coach? An easy way to get started is to ask for advice on some particular point, and grow the discussion out from there over a few weeks.

If you manage two people, you should still have time to code yourself. If you manage six or more, and have business/design/project leadership responsibilities, you probably won't have a lot of time for coding on average. If you manage ten or more people, you should split the people in sub groups and get managers for those groups. Verify changes with your VP before actually implementing them, but make sure you rub the agenda of your team.

Some times when people are self-taught, they lack confidence because they don't know what they don't know. This can lead to less competent colleagues, who happen to have a more aggressive personality than you, to move things in a bad direction. You sound like you have been entrusted with much. You probably know more than you realize.

It is critical to communicate your situation and needs to your VP. Unless you have immature management running the company, they need to know if you are drowning. Keep it objective (the metrics help with this). You don't want to come off complainy or the victim. Don't sugar coat the situation or be timid. You have some level of pull - the last thing your VP would want is for you to walk.

Don't ignore your health. Stress quickly becomes a vicious cycle, where once your willpower is depleted you make poor decisions, which only leads to worse stress. Whatever you eat, ask yourself what it is fueling. Get exercise. Unplug from work. Get enough sleep. See a doctor, or take supplements if needed. I had a big breakthrough in life when I started taking a supplement package. It pushed me over a tipping point. I was successful on a diet I had quit at least 30 times before, lost 40-50 lbs, no longer had afternoon crash in energy, and am much more productive even when I don't get enough sleep (I have a 1-year-old). My personal and professional lives improved significantly from getting my health in order.

Break down all the tasks you are doing and are supposed to be doing. Every task that you can see yourself doing for more than 8h/week needs to be done by somebody you hire.

Before you jump in and go on a hiring spree, make sure to list the top 5 outcomes (with measurement) you want to achieve by hiring this person. It also helps to list the personality traits/skillset you think they will need to achieve those outcomes. Using this approach you know what you are looking for and frankly, this approach has helped me bring in people that completely own their domain and almost need no guidance (beyond the initial onboarding). Ironically the goal you should have as a manager is to make yourself obsolete.

For more info on finding and testing exactly these people, read http://a16z.com/2014/07/15/do-you-feel-pressure-or-do-you-ap...

It helped me set my world straight for all the new responsibilities as a tech lead (and I'm not a natural with pressure either, having learned the value of having a slight rough edge the hard way).

For more concentrated pure gold, look here: http://www.defmacro.org/2014/10/03/engman.html

In the end, your best bet as said is great hiring and pushing work away from you, which is hardest when you feel you're still doing and understanding it best yourself. Stop this anyway.

Great guideline from my co-founder: Try to get people 70% as good as you and stop there. Really try to lose as much day-to-day-stuff as possible and try rather to get the right people together and give them good context.

Get some senior people along to proxy all semi-important stuff through them. It's a quick way to get them onboarded to stuff you usually do.

Otherwise: Good luck, you could need a mentor, but it looks like you're alright for now, don't search too hard. Don't be too scared of doing mistakes either, you'll do them anyway.

But do yourself a favor and go get that title upgrade to whatever you need (Tech Lead / Lead Architect) - you'll have to be sure you've got the upper echelon's support to whatever uncomfortable decisions you need to take on the way.

Also: Look to promote people who already work for you. If you know someone is good that is much easier than hiring an unknown.

Also: Delegate & follow up.

I would recommend the book "essentialism".

You can't do it all. You need to define what is the most important things and avoid everything else. This is how you get balance and reduce stress.

I've had experiences almost exactly like yours. Long hours, lots of pressure from above and below.

I have found that leaving the office and wandering around our neighbourhood for a few minutes (<=10 && <=30) when I'm feeling loaded really helps clear the brain.

What's neat is that when I come back I can usually find one thing I need to knock out from my massive list and close it, done well. It's like I come back with clarity and energy. Of course it depends on making it from the door to your desk before anyone says "do you have a minute?" - then it all goes to heck for me.

I also "escape" at the weekend. Clearing head-space like that puts you in a good mood, lets your sub-conscious solve some of the issues.

Happy people are better workers. Remember that for yourself and more importantly for the team you manage.

First step is to determine proper team size to do the job. Next bring in a few key teams members who you can trust to get things done. Start delegating stuff. However try not to delegate the understanding of the overall project. You should have a good pulse of how things are progressing without polling people. That mean being in code reviews, reviewing commits, etc.

There are a number of good suggestions here about how to make the best of what you're doing; My suggestion is to look closely at how the job feels while you're doing it (as opposed to how it feels when you're telling people about your role). You may find that being a senior engineer or architect minus the planning, tracking and administrating makes for a better work-life.

I know I did.

Either promote from within or hire some junior managers - e.g. HR, etc. Work out what needs to be done and delegate. I presume you like the architecture design, etc. Once you delegate (and hold responsible) others for the roles that you do not enjoy and do not have bandwidth to handle, you can do what you enjoy.

Remember it is easier to ask for forgiveness than to ask for permission. You might be surprised to discover that you were being tested to see if you could step up. You DO NOT need to learn how to do it all, you simply hire competent people to do what you are unable to.

The first thing to remember is you will always "be personally tasked with building out the product" and you will be doing less and less of the actual coding, but you will still get fired if the product fails big time. In theory the extra risk come along with extra pay, since this sounds like the first time you're doing this I'm guessing you may find you aren't being paid commensurately with the risk you are taking.

As you become senior leadership, your task is to look further and further ahead in time and try to anticipate, and have plans for the various situations that may arise. Given that those situations will have various chances of actually coming to pass, those that are unlikely you can just sketch out an idea for a plan, those that are more likely you need something more detailed. One of the secrets of being a good leader is that while it may seem like you "pulled a great plan out of the air when this thing happened", its really that you had already considered weeks or months ago what you would recommend if that weird thing happened.

As you get closer to the top you will have to include business priorities as part of the "weird things that can happen you have to look out for." and to understand exactly how the company is generating value using the products or services your team is developing or providing. Nothing is more frustrating to a brilliant engineer than to deliver a beautiful architecture and product to a company that cannot use it in their business when it is delivered.

You should probably have a discussion with your boss, and your boss' boss in the same room talking about what you're going to be working on and delivering with your team. It will help tremendously down the road. That is also a good time to ask for training resources as your boss' boss will be eager to fund them if you are being successful and that will encourage your boss to actually provide them.

There is a weird point you can get to when you realize that you're boss is afraid of you, depending on your boss that can be very uncomfortable.

If you want to be a manager then you need to delegate most of the technical stuff. Not necessarily at the architecture level, but you really shouldn't be doing things like coding or writing estimates. You may be good at that kind of stuff, but other people are good at that kind of stuff too. Hire one of them.

The worst managers are the ones who can't let go of the technical work and half-ass the important part of their job, which is to manage.

The best suggestions (although you can find some great ones here) that I've received that helped me keeping afloat have been:

- don't overwork yourself, 7-8 hours a day is enough - plan ahead - keep a small to-do list of (top) three achievable things to be done by the end of the day - outside of work, focus on things that makes you feel better, like good friends and manual hobbies - get a good night sleep - eat heathy

Hope this helps.

Ask yourself, what it is that made your superiors put more responsibility in your hands. Find the capability that made you diffirent from your coworkers. Hold on to that, this is your differentiator. It's too easy to forget what is your differentiator when you advance quickly.

Recognize that you are now a manager and you are responsible for deciding what you are doing yourself and what you are delegating. If you are below VP level you will have to delegate almost everything even if you think you have to do it yourself. Try doing only one important thing each day. This important thing may be preparing speach, presentation, focusing on helping a project behind schedule, etc. Delegate everything else recognizing your limited time.

Recognize that, being a manager, your biggest responsibility is as enabler for your people. Empower your people, make them feel important, make them feel you trust them, and delegate things that are important and you may have hesitated delegating up to now. Hiring plans, work estimates, gap analyses, etc, do you think you have to do it all by yourself?

Find some management advice. As a fresh manager myself in very similar situation to yours (large part of organization and very important projects bestowed in very short time from my coming into organization) I like to listen to management audiobooks like Harvard Business Review and the likes. There is a lot of very good advice but the most important part is that you are actually aware what can go wrong in your current role so that you can recognize the problem and act on it before it becomes full blown disaster.

Most important, if you think something stresses you, stop and think. Don't let the stress overcome you, but spend on trying to understand what part of the task is stressing, why is it stressing and what could be done to remove stress. Don't let the downward spiral take you.