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I'm the admin assistant of the CTO and our organization has recently experienced a lot of growth. Within six months, we have merged with another organization and our Dev team has grown from 8 to 16, with another 8 people in QA.

What we're dealing with now is a highly technical individual, with little patience, managing a much larger team than he's accustomed to, 40% of which is junior as well as an increase in the number of projects. Needless to say, my boss is being pulled in too many directions at once. How can I help him manage his workload and his team so that the team feels they're getting enough help and support and remain effective?

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Might be quite relevant... workplace.stackexchange.com/questions/2986/… –  enderland Aug 28 '12 at 19:41
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Your boss should NOT be doing any technical work at all. He should be managing other people's work. So first, he needs to drop all developement he himself is doing. That will likely free up some time. –  HLGEM Aug 29 '12 at 19:16
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2 Answers

  1. Talk with your boss about whether he could delegate any of his work. He doesn't have to create permanent levels of middle-management; can he appoint a tech lead for each key project and let those people handle the day-to-day stuff?

  2. Try to identify tasks that could be off-loaded entirely, and candidates within the organization who could do them. When my current company was small the engineering manager interviewed all candidates; as we grew that became unworkable, and now we have a few developers who are in charge of the interviewing, with permission to draw in others as needed, and the manager interviews only the most-senior, business-affecting candidates. Identify the things "like that" in your organization, the things your boss is involved in "because he always has been" rather than "because he needs to be", and help find other ways to get those things done.

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I have heard this called "managing up," and it's usually illustrated by having a staffer ask their manager, "What can I do to make you successful? In your case, if you propose having your boss delegate some things to you (or whoever), that will free up some of their time to actually make progress. If you have time to do it, it's great for you and for your boss. Everybody wins! –  Will E. Aug 29 '12 at 15:00
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Your boss sounds like a senior dev or team lead acting as a CTO; in most hierarchies that puts him at least two levels above his pay grade. It sounds to me that if you have a CTO who is focusing on the small details and is being overwhelmed by them, he needs to grow into his position a little, and adjust the "zoom level" on his corporate magnifying glass, to focus on the people, the teams and the big picture, not the minutiae.

The first thing I would do as the CTO is identify the functional teams within his hierarchy. Those 16 devs and 8 QA are probably more like 2 groups of 8 devs and 4 BA/QA. I would identify what they're working on and who's working on it, name these as teams, and appoint someone to be "team lead". If there are two or more "teams" working on the same overall "project", consider a "project manager" whose job it is to oversee the day-to-day of both teams. This is a judgement call and can be quite political, especially picking someone over someone else of equal or greater perceived qualifications (experience, education, seniority, skills). So it probably won't be an easy call, but that's why he's the CTO; he gets to make the tough calls.

With that sorted, the CTO's job is to manage the teams through the team leads. At its most basic, the job of every worker's supervisor, from the senior dev to the CTO of the company, is to make the decision that extends beyond the scope of the worker's own control, thus removing the hindrance to their work. A junior coder pretty much can't make a decision in his work that affects anyone beyond himself; a senior dev can affect the path of the junior coders he supervises. A senior dev can't make decisions affecting the entire team; a team lead can. A team lead can't make decisions that affect other teams; a project manager can. A project manager can't make decisions that impact the entire business; a CTO can. Here's the rub; a CTO shouldn't be making the decisions that affect only one senior dev and his juniors. That's the team lead's job. It's when the team lead and/or the project manager can't solve the problem that they bring it to the CTO.

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