Has Your Boss Set You Up To Succeed or Fail?

A reader asked recently (see the archive):

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 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 and discuss them with you. Second, they invest their own time, in coordination with you, clearing a path for those tasks to go more easily, or to become possible at all. A good boss builds a runway for you so that you can smoothly take off and checks in while you’re in the air, making adjustments behind the scenes, so you and your projects will land safely too. But taken too far this becomes micromanagement, which is the inverse way to set up someone to fail because the manager is far too involved. A good manager finds the sweet spot for each person and situation.

You know you’re being set up to fail if you’re assigned a project that:

  • No one seems to know about
  • Other people believe is their project or decision
  • Everyone treats as low priority

When there are major hidden obstacles on the runway, people telling you the runway is theirs and you’re not allowed, or there’s no runway at all, your manager is setting you up to fail. You are being managed poorly.

One exception is that they have clearly warned you about these conditions before you agreed to take them on (perhaps you’re a secret agent), or made clear they themselves have little knowledge of the landscape and part of your task is to map it and report back, they are either incompetent, indifferent or see more benefits in your failure than your success.

The checklist for assessing your situation

Here’s a simple list of questions to discuss with your boss (or at least with yourself) to assess if you are being set up to succeed or not. 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 and how that stacks up against what the project requires?
  2. Do I have the right allies? Who has the power you need to do your job and are they on your side? Will they prioritize your requests? Invite you in to decisions early enough to be effective? A good boss will talk to other important people in the organization about your goals and create an agreement for how you all will work together. Or at least call out the roadblocks they can’t resolve so at least you know they are there.
  3. Do I have the right resources (power, budget, staff, time)? You may have the right skills and allies, but if you don’t have enough power, time or money to do the work, you’ll likely fail anyway. The goals of the project might need to change if the available resources can’t.
  4. 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? Listing non-goals, things easily assumed to be goals, but are really distractions, can be just as important to discuss.
  5. Are senior management’s goals aligned with the ones you have been given? If not your success will depend on you working against the grain of the organization and you are likely to fail. 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? Have they at least agreed you are on a high risk mission and even a small amount of success will be an acceptable win?

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. If you are continually set up to fail and don’t feel you are getting the proper amount of support, you have a bad manager. You should find a new one if you can.

Of course, depending on the job you have, and how senior your role is, you may be expected to identify and solve many hard problems on your own. It may be possible for you to create your own runway through influence, persuasion, relationship building and negotiation. These are valuable skills and are often necessary even if you have a good manager, but become critical if you are working for a bad one.

Some organizations call this “Dealing with Ambiguity” or “Organizational Agility.” While it’s true more senior staff should be able to handle more challenges on their own, there are limits. The expectation of all good managers is that as the boss they have more responsibility and power for making good work happen and if they fail to use it to help everyone on their team they are simply not doing their job.

What else can someone do to help in these situations? Leave a comment.


14 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!

  7. Iren

    Great post, thanks! It’s actually made me think more of my own employees since I don’t have the boss anymore

  8. Alison

    What a wonderful article. I’ve been searching the web currently as I have been (along with some other colleagues) set up for failure. The thing that I find the most troubling with these sorts of managers is that they don’t seem to realize that they succeed when we succeed. We rise by lifting others. When we fail, it reflects on them and their leadership. I currently don’t have many of the tools I think I need to do my job and I have also found that my boss and her boss are ill-equipped to be in their roles, so it’s a bit like the blind leading the blind. Not a good combo!
    Anyway let me say this again – we rise by lifting others!

  9. Arthur

    My boss definitely has set me up for failure. I was hired based on my skill set and never in the interview process did the question of exactly the type of work ever come up. I am expected to provided analysis of a business which results in flow charts, diagrams etc. but no where in the interview process was this mentioned for an IT / Laboratory Solution position.
    As a manager and hiring manager, I always asked the technical questions about the work I expected to be done and could the candidate handle this work base don what they knew. Mangers like mine seem to be ego filled with looking for good candidates based purely on a resume. These managers are incompetent as a person must be able to do the work. I have found it is almost non-existent that a person I hired was unable to take on their responsibilities. Big pharma is chiefly responsible as is very small startups. Mid range companies tend to have better hiring practices where HR is strongly involved.

  10. Henry Leo

    Thanks for sharing. I have been troubled with my career & now i know why.

  11. Henry Leo

    Thanks for sharing


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