Get my email lessons on how you can build a tech team you can depend on.

Who’s your Bob?

At my last job, Bob was the DBA, SysAdmin and SAN Manager. Bob had been there forever, mostly kept to himself, and knew how most everything worked. He’d worked for many different bosses, outlasting them all.

One day about 14 years ago, I asked Bob, “What would we do if you ever quit, Bob?”

“It will take at least four people to replace me,” he said with a grin. We both laughed.

Friday I learned that Bob was still at the company, doing the same job, all alone. It’s not unreasonable to think that it could take six people to replace him now, or more. He hasn’t been promoted, doesn’t have a team to train, and isn’t paid particularly well.

Bob will probably never quit, but he will retire at some point. Or, have a stroke.

When he does, twenty years of tech debt will come due. There won’t be a payment plan, it will all be due right-now.

Tech debt like this is a failing of management, not technical teams.

For twenty years Bob’s managers and the VP of IS, the CTO, and the entire board of directors have turned a blind eye to the debt they were racking up.

Most everyone in IS knows about it, but just shrugs. After all, if Bob’s not complaining, why should they?

When Bob leaves, voluntarily or not, the company will be screwed. Managers who think they can hire someone to come in and “figure out how it works” are going to have a hard time.

DevOps is not the answer

Please don’t write me back that DevOps is the answer, it’s not. That’s missing the point.

Some of you have people on your team who singlehandedly carry decades of knowledge, but I want you to understand it’s not an asset. It’s a liability.

It’s a debt that you can start paying off today, or you can wait until your Bob leaves, and pay it off at a much higher interest rate. But make no mistake, the debt will be paid.

Does this sound familiar, or am I crazy? Do you see any Bob’s where you work?


About Marcus Blankenship

Where other technical coaches focus on process or tools, I focus on the human aspects of your Programmer to Manager transition. I help you hire the right people, create the right culture, and setup the right process which achieves your goals. Managing your team isn't something you learned in college. In fact, my clients often tell me "I never prepared for this role, I always focused on doing the work". If you're ready to improve your leadership, process and team, find out how I can help you.


  1. Bob Erb on April 8, 2019 at 11:36 am

    How might one go about starting to pay off this sort of technical debt? I’m afraid I’m a bit of a Bob myself, and don’t want to leave my current employer too many problems when I leave.

  2. Rick on April 12, 2019 at 8:50 am

    Marcus, we had a ‘Bob’ at our company and we’re still paying off that debt. He only left about 6 months ago, and some of us were familiar with what he did, but none of us “knew” it as well as he did. He designed it and was the main support. It’s fallen to me to take up the slack as well as be a sort-of Bob myself as I am currently the only one doing what I’m doing. Full disclosure: we are trying to prevent this from happening again. We are trying to cross-train so the person who is my backup can at least know enough to not be slapped in the face. We’re trying to prevent the one-point of failure situation.

  3. Neil on April 12, 2019 at 10:49 am

    @Bob Erb – Seems you most certainly are a “Bob” 😉

    Firts off Kudos for your instincts and attitude!
    You need to start training a successor (or partner) – Ideally it could be more than 1 person to spread the risk.
    I suggest:
    * A working agreement and a trello board that shows the responsibilties being transferred.
    * A deliverable of documentation (say a wiki) – you write the first draft for each area of responsibilty. You support your successor in completing the tasks independently. Part of being done is that the successor enhances the docs each time they hit a WTF moment.

    There’s a great talk given by Kevin Goldsmith with many ideas:

    BTW: I’m proud to say I’ve made myself dispensaible in a number of roles 🙂

Pin It on Pinterest

Share This