how to help staff members step out of their comfort zones

Helping your team members develop their skills can pay off in all sorts of ways: They’ll get better results in their work, be able to shift more and more work from your plate to theirs, and will generally stick around longer and feel more fulfilled when they can see themselves growing professionally.

But what do you do when staff members are nervous about taking on something they’ve never done before and don’t know if they’ll succeed at? Here are four ways to help employees step out of their comfort zones and develop new skills.

1. Err on the side of letting your staff members make decisions whenever you can. Managers sometimes get so used to making decisions that they forget to step back and let team members make decisions when circumstances allow for it. If you’re asked to weigh in on something and you don’t feel strongly about the decision, hold your tongue and instead leave it up to your staff member. If you’re always calling the shots yourself, your staffer won’t get experience thinking through decisions – which is essential to doing higher and higher level work. So when you spot opportunities to pass that decision-making responsibility along, do it. Get comfortable with the words “It’s up to you” or “What do you think?”

2. Give people stretch assignments and tell them why you think they’ll be able to handle it. Assigning projects that require developing new skills (or using old skills at a higher level) is one of the best ways to develop employees, since most people learn by doing. But in order to make sure your employee doesn’t feel thrown to the wolves, make sure to explain why you think she can handle it – such as by pointing to great work that she’s done in a similar area, or talking about strengths you’ve observed in her that will help her tackle this new frontier. Additionally….

3. Use a gradual approach. If your staff member is daunted by the thought of taking on a whole new type of work that she’s never done before, make it more manageable by breaking it into smaller pieces. For instance, rather than just a staff member in charge of training new employees, start by talking with her about how you normally train people, what it looks like when it goes smoothly, and what the pitfalls are. Then let her sit in while you train someone, or jointly train someone together. Then the next time a new hire needs to be trained, you might have her manage the process, but look over her training plan and reflect with her afterwards about how it went. In other words, ease people into new areas gradually, before you expect them to do it on their own without help from you.

4. Model the skill yourself – and talk about what you’re doing and why. Often people need to see and reflect on how a skill is used before feeling comfortable doing it themselves. So if, for instance, you’re trying to help a staff member get better at running strategy meetings, you might have her watch while you lead one. Then, afterwards, meet to talk over what you did and why, such as how you got the group to agree to an agenda at the start of the meeting, why you left a particular tangent run its course while choosing to redirect another one, and how you drew out quieter members of the group. This type of watching and reflecting can help people feel much more prepared to practice the skill themselves.

I originally published this at Intuit QuickBase. 

{ 27 comments… read them below }

  1. EngineerGirl*

    You forgot a major one – giving them room for failure. It’s a stretch assignment after all, so it won’t be perfect the first time. So many employers penalize someone when it isn’t perfect. It affects their reputation. Here’s the irony – the people that make mistakes know how something could fail. That means that they know more about the product than the people that might have accidently got it right the first time (or got extensive coaching). In addition, the people that failed on their fist attempt know the signs and warnings for future projects.
    You only become an expert when you not only know how to succeed, but how things fail.

    1. Pontoon Pirate*

      This is exactly what I wanted to say. Give your people room to fail and let it be known that you understand failure is part of growth. That doesn’t mean excusing lazy work or using failure as a crutch. It means you’re creating a culture where people want to develop and excel because they know management understands that sometimes growth starts from failure.

    2. Sharon*

      Also, people who see that a coworker did some stretch task and fail and get punished for it will also not ask for stretch work. Punishing failure for one person inhibits your entire workforce from stepping outside of their comfort zones.

  2. MM*

    I’m 25 and my boss has been amazing at this. She usually throws me into a project and just kind of has the attitude of “Just do it, no excuses, tell me if you mess up. We all mess up at first.” We have follow up meetings to talk about what I did right and wrong, and she’s not shy about telling me what she didn’t like. She’s very tough but very fair. When I admit to my mistakes, they are always forgiven. If I try to play them off or sweep them under the rug, she gets really mad. It’s taught me to not be afraid to fail and not be afraid to ADMIT to failing. I used to work so hard to hide my flaws at work, and I see now how immature and unhelpful that is.

    I’ve made so, so many mistakes at work, and my job often stresses me out a lot, but I have grown so much that I feel like a totally different person than I was a year and a half ago.

    1. PumpkinEverything*

      That’s amazing – I wish I had more employees like you. What a wonderful attitude!

  3. Miss Betty*

    I think a much better question would be how can employees convince their managers that they want to step out of their comfort zone, develop new skills, take on more and different assignments? I’ve seen – over the course of my working life, in three different fields, and in many different organizations – far more employees who are willing to stretch than employers who are willing to give them the chance.

    1. Sharon*

      That’s my experience also. In fact, my entire career resulted from this: that is, each time I looked for a new job, I leveraged what I knew best as career advisors say to do (in my case Cobol programming), so every job I took was just more and more Cobol programming. I learned other stuff in my own personal time but was never able to convince hiring managers to hire me for them. A few years ago I finally escaped the Cobol prison by repositioning myself as an IT business analyst.

      By contrast, I’m doing amazing things in my volunteer work. Accounting and light finance, leadership (I’m on the board) and volunteer management, public speaking and mentoring, event planning and organization, website development, all kinds of fun things that are really stretching me. Simply because there isn’t anybody to tell me I can’t do those things! At this point in my life, my paid job is just a job, but my volunteer work makes me feel like I rock the world!

      1. Not So NewReader*

        I totally get what you are saying about volunteering. I have grown more and faster from my volunteer jobs than I ever did at my paid jobs.
        I will say that it has been handy to say to a boss, “yeah, I have done that before for my volunteer work so I know I can handle this, too.” Then watch the boss’ eyebrows go right up.

      2. yarp*

        I’m in the same boat. In my first job, I found that I’m particularly good at this one thing. Two employers and 7 years later, and I’m still doing the same stuff. I have asked for exposure in other fields, and promises were made, but nothing ever happens. One time I was able to actually start on something else, but then my manager told me to let someone else handle that, because they need me on The Thing I’m good at.

        After 7 years of doing the same work, and not getting any opportunities to develop, two things are happening:
        1. I’m getting penalised for not showing enough development.
        2. It becomes more difficult to be able to find a job elsewhere.

        I’m stuck

  4. brightstar*

    Has anyone dealt with an employee who doesn’t want to grow and has made it clear their career isn’t their priority? Not someone who slacks off at work, but whom absolutely refuses to leave their comfort zone and passes for chances to increase knowledge or responsibilities?

    1. OriginalYup*

      I worked with two people like this, at the same job.

      Kate resisted until her boss made it clear that she had to do so if she wanted to keep her job. Because we were launching a once-in-a-decade all-hands-on-deck company project where *everyone* had to go outside their comfort zone in order to have enough bodies get the work done. She did it begrudgingly, but she did it do, and seemed to have a more positive attitude about it after that initial adapt-or-die experience.

      Steve just keep passively resisting until his name was mud throughout the company. Everyone was frustrated with him because his refusal to get on board meant more work for the rest of us. He probably would have eventually been forced out if he hadn’t left of his own accord.

      1. Scott M*

        Sounds like project I was on once. But in this case it was more than “go outside your comfort zone”. It was more like “no one else knows what to do either so just keep running as fast as you can until someone tells you to stop”.

        I did not take to this well, but managed to muddle through. Since then, If I need to step outside my comfort zone, I’m going to have a pretty clear idea of what that means first.

    2. PumpkinEverything*

      Yes, absolutely. I have a senior level person who was complaining that she didn’t have enough to do. When I offered her the chance to stretch herself and in turn become more visible within the company, she flatly refused. When pressed, she said she just wasn’t willing to do anything that she didn’t already have expertise in (regardless of me pointing out that this new function was an area in which NO ONE had expertise). Eventually she got the point that this new skill would help her in the long run and that turning down new opportunities for growth, while at the same time complaining, was not a good move for her career at our company. It was like pulling teeth, though.

      I have another employee who took on new, major responsibility and at the end of the project determined it just wasn’t for her. I respect her for pushing her limits, and for understanding what her limits are. Not everyone needs or wants to develop in their careers, and every team needs steady worker bees in order to function at its best.

      1. Not So NewReader*

        Sometimes people do not want to grow in the ways that the company wants them to grow.
        “No, I don’t want to learn to do root canals every Thursday. I have no interest in dentistry.”

        This can be a defining moment in their career path, forcing them to realize that they need to go in another direction.

  5. ClaireS*

    This is great advice.

    I’d love to see the advice from the other side: how to be a great employee when given a stretch assignment.

    1. PumpkinEverything*

      I can give you my perspective as a manager. First off, I think it’s normal to be intimidated (just as it’s normal to NOT be intimidated) by a stretch assignment so while I wouldn’t expect strong pushback, I don’t think it’s unusual for someone to ask a lot of questions when presented with a stretch assignment. In fact, if the questions were thoughtful and relevant, I would be very pleased. It depends on the manager, but I personally would expect that employee to check in frequently to provide updates, ask questions, and present possible solutions to challenges. I think it’s important (always) to discuss type and frequency of communication when taking on a new responsibility or challenge. For example, if your boss is very hands-off (and let’s hope that’s not the case in a stretch assignment situation) or extremely busy, he/she may not appreciate daily updates or questions but you could negotiate the frequency of your interactions, or even ask if there is someone who could mentor you in the new process. I hope this helps!

    2. Not So NewReader*

      I have done some supervisory work and oh-so-much training. So this is an answer from that perspective. I briefly explain the task as an overview- this is what it will look like when it is done.

      Most tasks have a point of no return or a point where a redo is a major PITA. So I try to build a stop into the task just before the point of no return. “Do steps 1-8, then stop and come see me.” I usually explain why that is a good point to do so- “If you stop there we can check it together, that is an easy place to correct problems.”

      I tend to hand out fishing poles not fish. So my check of their work is to show them where common errors occur. I talk about how to fix these errors.
      This is all time consuming but I end up working with people who stand on their own two feet quite nicely. Not applicable to every setting, clearly.
      The best workers were the ones who came back to me as planned. If they had a problem before that they would also come find me. Annnnd, the best people were the ones that looked for patterns and reported anything that did not fit the pattern they were accustomed to. (Meaning things that made no sense, they did not try to force the issue but instead opted to tell me “I tried a, b and c and I just cannot get it to work in this instance.”)

  6. Avocado*

    In some environments, I’d say that part of the problem is convincing coworkers that the staff member stepping out of their comfort zone is capable enough to take on a “stretch” assignment.

    I’m running into that problem myself. For a couple years, I’ve really only been doing a subset of what’s in my job description. It’s started to box me into a specialist role that tends to have little career progression and is more “back-office” than what those who share my job title got to focus on. My boss has started to give me increasing, more visible responsibilities that are more in line with what my coworkers do. That’s great, and I think I’m capable of taking on new challenges, but I’m not sure that my coworkers feel the same way. They seem to pigeonhole me as having a more junior niche and don’t really look to me as someone who’s capable of anything bigger-picture. I get some of the issues at play – they’re all guys with graduate degrees, while I’m a slightly younger woman with a BA, but lots of relevant experience. There’s no good reason for them to think I am capable, right? One of them, while well-meaning, comes across pretty officious about whether I “need help” and acts like he needs to step in and clean up my messes. How do I get them to be as on board with my career progression as my boss is?

    1. Not So NewReader*

      You go one person at a time. And be your professional self every moment of the way.

      I have found two routes here that seem to help.
      Route number one is to build positive working relationships with the easier people. Let rumors and scuttlebutt do their thing. “Gee, I was working with Advocado on X and boy, she had some [insert compliment here- great ideas, massive organization skills, did quick and accurate work].” Let the rumor mill take care of the problem for you. Officious Bob will become the lone voice questioning your ability while everyone else is saying it is a pleasure to work with you.

      Route number two is to take the bull by the horns and speak directly to Officious Bob. “Bob, I am new at these particular tasks and I fully expect to make mistakes. However, I also will take full responsibility for fixing my own mistakes. After all, that is how WE ALL learn to do our jobs well, ISN’T it, Bob?!” Repeat as needed.

      I prefer Route number one because this frees me up to just concentrate on learning my job. But if Bob does not let the subject die a natural death, then I have to say something.

  7. Mimmy*

    A big fat Amen to #3!! I know many employers are stretched thin either due to lack of time or lack of resources, but don’t just throw me in with piles of stuff to read without scheduling some time to actually go over it with me! Also, how ’bout I watch someone else do this, then watch me do it so that I know I’m on the right track. Okay, you probably thought I knew what I was doing, but that other setting was way different from this one!

    ^^ In reference to a previous job, not anything current.

    1. Not So NewReader*

      State government officials this means YOU. Don’t give me books covering six feet of shelf space and then not give me any time to read them.

      /rant. I feel better now.

      1. Mimmy*

        LOL I had time to read all the material and even watch videos, maybe two weeks? It was just all self-study with maybe one or two meetings (that I can remember) with my supervisor to go over one specific topic. There was no real structure to it at all.

  8. Scott M*

    I’d like to point out that all of Allison’s involve *easing* employees into something new. Too often managers think that ‘stretch goals’ mean “assign the impossible and see if they sink or swim”.

  9. Another HR Pro*

    Part of this is knowing how your employee responds to this type of stress. I personally love sink or swim assignments. That is when I do my best. I enjoying figuring out how to solve something that hasn’t been solve before. My staff is not that way. Some of them prefer structured challenges and others simply resist any work that is uncomfortable. So my strategy is different with each of them.

    1. Scott M*

      You sound like a good manager. I know a lot of managers who love the sink-or-swim challenges. The problem is that they think EVERYONE loves the same thing (and if they don’t, they aren’t good employees). Luckily my current boss is not like that. But I’ve seen many who are.

    2. Not So NewReader*

      This. Different techniques for different people. I had a person that was absolutely terrified of a new machine we had. Loooong story made short, when I finally got her to use the machine I did not say anything about the drama due to fear. Instead I addressed how part of my job was to keep everyone safe on the job. I told her that it was totally acceptable for her to ask, “So, boss, what is the safety plan for this new machine?” I told her not to allow her concerns to drag out for so long, she should come talk things over with me rather than torturing herself.

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