Has Your Boss Set You Up To Succeed or Fail?

On Tuesdays I write about the top voted question on Ask Berkun (see the lovely archive). Yes I know it’s Thursday, but better late than never. Here’s this week’s question:

I have a new boss who I don’t trust yet. How can I make sure they’re looking out for me?

The term “set up to succeed” means a person has been given most of what they need to do their job well. A good boss does more than just set goals and give assignments: they should see themselves as responsible for ensuring good work happens (See: Lefferts Law of Management). First, they think through the steps that need to happen for someone to do a project and where the challenges are going to be. Second, they invest their own time clearing a path for those tasks to go more easily (so higher levels of performance are possible). A good boss builds a runway for you so that you can smoothly take off. Alternatively, you know you’re being set up to fail if you’re assigned a project with impossible odds, conflicting goals or a fraction of the resources required. When there are major obstacles on the runway, or no runway at all, your manager isn’t doing their job.

Here’s a simple list of questions you can ask to see how well set up you are to succeed (or fail). They can be used to structure a conversation with your boss about what you need and why.

  1. Do I have the right skills? If you’re told to pilot a Boeing 747 but you have never even flown a paper airplane, whose fault is it if you fail? What training and mentoring is provided to help close skill gaps? Does your boss understand what you can and can not do as well as what the project requires?
  2. Do I have the right resources (budget, staff)? You may have the right skills, but if you don’t have enough time or money to do the work, you’ll fail anyway. The goals of the project might need to change if the available resources can’t.
  3. Are there clear goals (and non-goals)? Clarity on desired outcomes is one of the most important things a leader provides. Does everyone understand and agree on how you’ll know when the work is done and that it was done right? A non-goal is something that’s easily assumed to be a goal, but should be avoided.
  4. Do the people you depend on have the motivation to help you? You may need several people to get work done before you can do yours. Will they prioritize your requests? Help make sure you have what you need? A good boss will have talked to other staff in the organization about your tasks and created an agreement for how you all will work together.
  5. Are senior management’s goals aligned with the ones you have been given? Your odds of success are much higher if your individual goals line up with those around and above you. If they don’t, you’ll be working against the grain of your organization. A good boss has made sure the right senior staff know about your projects and that all the goals line up.
  6. What roadblocks are in your way that you do not have the power or skills to resolve? Who has been made aware of them? Who has the power you need to resolve them? Has your boss worked with you on a plan? Have you warned the right people of what may happen if the roadblock is not cleared?

Incompetent managers often unintentionally set up their employees to fail. They don’t realize they are giving conflicting goals, poorly allocating resources or that they’re asking people to take on work that is politically sensitive and possibly damaging to their reputation. This means you have to advocate for yourself, first by thinking through the challenges you’re going to face and second by involving your boss in helping you clear them out of your way.

Of course, depending on the job you have, and how senior your role is, you may be expected to identify and solve many problems on your own. Some organizations call this “Dealing with Ambiguity” or “Organizational Agility” and think of it as a skill. It’s true that stronger employees can handle more challenges on their own. However, the reason why managers are paid more is that they have more responsibility and power for making good work happen. If they do nothing to help their staff succeed, they’re simply not doing their job.

What other ways have you seen managers set up their employees to succeed or fail? Leave a comment.



9 Responses to “Has Your Boss Set You Up To Succeed or Fail?”

  1. Ben Cotton

    Great set of questions. The trouble I’ve had in my career is not even knowing enough to be able to evaluate the answers. But most of my jobs have basically involved me jumping into the deep end and hoping I learn how to swim.

    1. Scott Berkun

      Yes! I tried to hint at this at then end, but for the ambitious a good job means much is undefined and needs you to define it. It’s a tricky line for where a manager is bad vs. where they are giving room to grow.

  2. Michael LaRocca, Business Editor

    Replace “boss” with “customer” and that’s my life right now. But when I finish this edit, I won’t ever work with that author again. Changing bosses is harder than that.

    1. Scott Berkun

      Yikes – I suppose the bright side is unlike a boss, with a customer there is no expectation for the relationship to continue :)

  3. Jim Hunt

    Hey Scott.
    As a manager myself I can say that the whole range of freedom vs. specificity applies when working with a diverse team. Some people need a lot more hand-holding than others. Some need very little, and won’t continue to grow otherwise. Some level of challenge (discomfort?) is required for people to move forward. Put differently: When you think back (i.e. over the past year), do you feel good about your progress (skill/ability growth, making your resume stronger, etc)? I think without some level of challenge it is hard to answer “yes” to that question. But the desirable amount of challenge varies from person to person, and a good boss must find the sweet-spot for each individual.

    Also at minimum, a decent boss must keep career goals and interests as part of ongoing conversations, and provide support – even if those interests take them off of the current team in the future. “Support” can mean accommodation (at minimum), or (best) delivering growth opportunities.
    A really GREAT boss also offers suggestions for growth that a team member might not have considered or realized, by observing their interests and behavior through the lens of experience.

    Unfortunately, the vast majority of managers, at least in the Tech-Industry, are woefully under-trained, and unburdened by the skillset of a good manager. Too often people who are technically skillful are asked to be people-leaders also, with zero experience and little or no training in that field… Keeping in mind many top techies have (ahem) lower than average natural skills in communications and leadership. And in any industry, even a great manager can be compromised (have their hands tied, so to speak) by their own leadership.

    I should add, as a great example of someone who started out my career with very poor “soft” skills, these skills are learn-able.

    If there is a one-liner for how to be a good boss, I think it’s this:

    “Be the kind of boss you’d like to have.”



    1. Scott Berkun

      I agree about different people needing to be managed differently. Better bosses know their own preferred style and help their staff figure out theirs as well. I learned it was good when I had a new boss to directly tell them my preferences and what to expect from me. It’s a good converation to make sure happens even if your boss doesn’t initiate it.

      > “Be the kind of boss you’d like to have.”

      That’s part of the way there – but like the golden rule, it has flaws if you have someone who has different needs/desires than your own. The Platinum rule is the way to go, which states “Do unto others as they would have you do unto them” which finally yields “Be the kind of boss best suited to the person you are managing”

  4. Sean Crawford

    I twinged at the phrase “don’t trust yet.” I think one’s default trust setting should be whatever helps one the most, and be aware if one’s setting doesn’t help. (people vary in their optimum defaults)

    I would treat Scott’s points like a pilot treats her pre-flight checklist. It’s irrelevant whether she trusts her ground crew to have filled the de-icing tanks, she checks her cockpit switch anyways, impersonally. Comprehensively and consciously.

  5. Smaranda

    I had a manger once who couldn’t even stay on top of his Outlook. Every time we had a meeting I’d have to go remind him and (not literally) “take him by the hand” and get him to the right meeting room. In the one year we worked together I don’t think he mastered the concept of proposing a new meeting time or reliably accepting invites. This would be the same person who would tell me to do completely opposite things on two different weeks and then come back and ask why I was going around in circles. I later realized (after quitting) that HE was the one who simply didn’t have the skills for the job – nor did he have the right mindset to aquire the skills. Which set the whole team up for failure. Not the first time I see this.

    I also had another manager who would use “talking people to death” as a strategy for pretty much anything that he disagreed with. It was practically impossible to run anything by him or ask him for a decision. The first thing you said that wasn’t to his liking or that reminded him of something that was an issue, he wouild just start on a rant or endless unnecessary argumentation until you walked out of the meeting room and gave up , usually over time. This would be the same person that would monopolize team meetings with rants about everything that was going wrong in the company. I tried to address this with the higher powers, and was asked “why is this bothering you so much?”. WTF?!?! So I tend to agree with the point in the previous comment: there’s a lot of management skills often missing in IT unfortunately. People get promoted as managers for completely different reasons than their actual management skill set – all the way to the very top.

    So I guess what I’m trying to say is: ask yourself not only if you have the skills required for the job but also if your manager and his manager have the skills required for their job… Or at least any chance of getting them within the next year. If the answers is a big fat NO, run for the hills.

  6. Jake

    Thank you for the post! After reading it I realized that my boss is really good one. Well, I know that, but now can tell for sure!


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