Fork in the Road

A situation that affects a lot of those in Information Technology is one where they have to decide which path to follow. Do I stay technical or do I move into management?

This is not a win-lose situation, and there is no right or wrong answer. Like any other choice you make regarding your career, you need to make the choice that will make you the happiest in the long run.

The Lead Up

Unless you got into IT later in your career, the fork in the road should not be something that is faced within the first few years of your career. Those first few years are important for a whole slew of reasons, one of which being you need to determine whether IT is something you’re actually going to enjoy as a long-term/lifetime career.

That fork in the road should be at a time when you’re deciding to dedicate more time to technical (re)training, or if you want to focus your efforts on developing your talents & getting trained on leadership and managerial skills.

Here we’ll explore the paths one can take when faced with that career decision.

The Technical Motorway


  • You really love your technology. That feeling of excitement when a new version of operating system is released. That feature long in beta is ready for production use.
  • You love solving problems. You crack that complicated bug and fix a long outstanding problem.
  • You can specialise. Depending on the field and the companies you want to work for, you can become a lifetime Network Engineer, DBA, Storage Engineer, etc.
  • Technology doesn’t talk back. The idea of having to manage staff, having those difficult conversations with them, and the prospect of firing someone is a complete turn off.


  • Never-ending learning curve. You’ll always be on the back foot of staying up to date and keeping your skills fresh and marketable.
  • Obsolescence. Similar to the above, one day your field may be an easy target of outsourcing or be made redundant altogether. How many tape operators do you see any more?
  • Locked in the engine room. Being in IT can often be thankless enough, and made all that much harder when you’re an unknown for those who can help with your career in the future.
  • Remuneration. You’ll have to realise under most circumstances, your ability to keep increasing your salary will eventually plateau and will largely be boosted by indexing only.
  • Ageism. It will be harder to find a new technical job if you’re suddenly out of work in your fifties, looking at another ten to fifteen years of work life before you can retire. It isn’t impossible, but be prepared for some difficult sells.

The Management Highway


  • You enjoy a sense of responsibility. You like being in charge of a team and a set of technical functions.
  • You enjoy keeping a toe in the water. You enjoy being around technology, but you’re rather manage those who are full-time technical.
  • More exposure. You’ll work a lot more with your customers, vendors and your management, which will help raise your profile and reputation.
  • Career prospects. Start managing a team of 1 to 5 people. If you do that well, you’ll have a better chance of securing a managerial role for a team of 5 to 20. A few years after that, 20 to 50 with managers underneath you, and so on.


  • The buck stops with you. While you share in your team’s glory, you also take the heat when things go wrong.
  • Too many cooks. Be careful when your company is looking to reduce the amount of managers. If you’re still in the middle management phase of your career, you may be in the firing line.
  • Politics. A reality of the workplace; you’ll have to decide who to placate and who to make unhappy, which battles you want to fight and those you will surrender to.
  • Difficult conversations. Managing is easy when your team do their job and there are no problems, but as a manager you need to be prepared to deliver bad news; whether it’s about performance, remuneration, or even simple yes/no requests.

The Hybrid Overpass

I’ve written previously about the differences between managers and leaders, but it’s important to state that you can be a leader without being a ‘manager’, in the sense of having people reporting to you directly. Just in the same way that junior and senior staff can be defined differently apart from just their age or tenure, there are those who wish to remain technically focused but who also display and demonstrate leadership qualities.

Moreover, there are plenty of companies who employ a more flat organisational structure (also known as a horizontal structure). Apart from a lot of small businesses who need to have managers who still roll up their sleeves to get the technical work done, giants like Google also employ such flat structures. For these companies, these structures rely very heavily on open, frequent communication between everyone, and enable those who wish to take on more responsibility to do so. These are the companies who rely on the leaders (little l) rather than the Leaders (big L; those with direct reports in the traditional hierarchy).


  • The best of both worlds. If you’re a passionate fan of technology but want also wear the leader hat, this is for you.
  • You’re one of the guys and girls. In a group of technical staff, you may be treated better by your peers if you’re in the trenches with them as well as handling interference with the Managers above.


  • Jack of all trades, master of none. You will have less opportunity to specialise in your preferred discipline(s) of choice.
  • Future employment. It may be harder for you to move to another company where such a hybrid organisation doesn’t exist, especially if you’re aiming to move into Management exclusively; you may be considered as inexperienced with managing people because of the lack of the “solid line” reporting model that you’ve been working under.
  • Workload. You’ll have to manage technical work as well as some of the leadership and management duties, such as performance management, vendor management, financials (raising purchase orders and reconciling invoices), etc.


No matter the path you wish to take, it is a decision that needs to be made with careful consideration. Talk to your boss about it, discuss it with a mentor or trusted friends, and take the time to figure out which is the best way to achieve the changes you want. And even if you decide to stay on the technical path, you need to plan how you’re going to keep yourself energised and your skills polished & up to date.

If you have any stories to share along these lines, I’d love to hear them.

1 thought on “Fork in the Road

  1. If you’re good at what you do you’ll eventually have to make this decision in your career.

    I’m a believer that you should constantly push yourself outside of your comfort zone to grow as a person. Take the tougher path, the rewards will be worth it.

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