Tom Peruzzi's thoughts on digital, innovation, IT and operations

Should I stay or should I go now?

Posted in development by opstakes on September 12, 2015

What’s the right timing for a CTO to leave? Is it at the end of the tunnel? When you see the first light shining? Or any time later? There are plenty of reasons why one isn’t the right for all the time of a company cycle. Some CTOs are pretty good coders needed the first time, other CTOs are good in organizing stuff and need the thrill to launch, others may be good in keeping an existing system up and running.

So how do you know and why is it hard to leave? We all tend to stay “as long as possible”, we get used to be there, it becomes part of our live. I’ve seen so many really good talents staying way too long just because …

… of private issues

… they loved their title

… they earned much more than currently paid in that segment

… their life-planing was already optimized

… many more

People tend to stay much longer than expected. Instead of demanding that the company should be happy to have me on board more people tend to be loyal to the company as they are happy to be there. If I know what I can deliver to the company why shouldn’t I stand up and show my value? If I’m good I will find a job anywhere else. So is being good the general rule? For sure it is! If I’m loosing the will to become better day by day, if I’m loosing my passion, I not only become replaceable. I become boring and the longer it takes the more I will try to hinder or stop others from developing in order to stay infront of them, I will more and more become an obstacle to the innovation capability of the organization. The more people like me are around the harder it is for the organization. I’m lost in my own organization. Instead of kepping the pace I start being a citizen of the corporation and I will have no will (and no need) to move.

So it should be our intention to keep on developing. If so we will be interested working in teams with a similar mindset, working on demanding but achievable goals and getting the chance to educate in advance for the organization and ourselve.

Are the corporate citizens “left”? Somehow yes, it needs a lot of time, love and passion from a true leader to stop their inertia and bring them back to business. In my understanding you need to change at least 40% of such an organization to bring pace to an acceptable range again and there is risk associated. Cultural change takes a long time and the risk to fall back in any crisis or abnormal situation is very high. You need true leadership attention for a very long time and there is no guarantee to succeed (for sure it sometimes looks easier to start from scratch in parallel again).

But there is real great satisfaction if you succeed and see your people changing attitudes and speed and coming back to the road of success. It potentially is what differs a good leader from a leader or manager, the ability to bring people back to speed by changing culture.

But what, if you succeed? Is it than time to say goodbye? Do you need different people for different stages? I’ve seen tons of CTO’s bringing their organization up to 20 but failing afterwards because they didn’t want to do all the management stuff or becoming that big. If seen great leaders helping the organization through a phase of crisis and I’ve seen CTOs staying for 10 years + in a very steady but important state. What I havn’t seen so far is a CTO starting as a founder and leading it up to 100+ developers and staying there even if the company became mature, if you know one feel free to ping me.

So finally when should you leave? When the time is right, maybe if you had a great success but the state of the company changed. If you start seeing your position as “normal” and self-evident or if you see stars or innovation champions fading away because the organization started to become slow. Create new space for new ideas if you leave for the good of you and the company.

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  1. ministryofdev said, on November 8, 2016 at 11:00 pm

    Nice article and good insights. Ancelotti (book: Quiet Leadership) also weighs in something he calls ‘the leadership arc’. My interpretation and recollection of this is:

    – In the beginning a new leader is in its honeymoon phase. Since everyone needs to adjust anyways, they might as well do it to his style. Here you can express most of the plans of innovation.
    – Then strong leadership comes, people will (have to) align and things go uphill
    – But as soon as things will go better, one can cut down on innovation and start performing operationally consistent. Here is where people regain their own voice and become corporate citizens again
    – innovation has been done, the product is clear, and someone (usually from up the ladder) will demand something that doesn’t comply with the person in charge, either ideologically or by general perception of the team. This will eventually close the arc, and initiate a new one elsewhere.

    * there is no concrete timeframe in which these arcs should occur, but usually these steps should indicate the stage the leader is in.

    Do you recognize this? And is this applicable to the arc as you describe it?


    • opstakes said, on November 24, 2016 at 6:57 pm

      Hi Tim

      interesting thought. Havn’t read the book but seems like it is interesting. There are some up and downs all the time and if you read Ben Horowitz book or others you will see some similar procedure. That’s why some even came up to divide companies in 3 different sets with different behavior and culture. The first entity dealing with the product till its MVP, the second dealing with scaling up and the third one with tweaking and globalizing. Different kind of people are needed for that kind of jobs and succeeding in the one is no guarantee for succeeding in the other discipline as well.
      And yes I recognize those phases and I think I know where I’m best in, but it took me a while to undertand, accept and like it 😉

      Liked by 1 person

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