I work in IT Audit and am currently mentoring a team member whom I hope to be my eventual successor as I move upward into a lead / supervisory position in my department. He shows great technical skills and is a hard worker, someone who can be relied upon to get the work done. His analytical ability and theoretical knowledge are excellent, a point I frequently compliment.

However, during the months I have worked with him, I noticed he tends to be excessively conflict avoidant and meek. To give an example, I was reviewing his work papers on BCP / DRP testing, and he accepted management's feedback at face value, retracting his observations that are objectively valid and would improve the IT response during a disaster.

In another example, controls over IT operations (Backup & restore, data processing among others) are weak and valid findings were found. Two examples:

  1. Inconsistent backup testing contrary to policy
  2. Inadequate SoD - operations personnel with access to system logs

When questions arose from management, this team member starts to waver, losing confidence. The end recommendation made could be stronger and hence probability of corrective action taken greater.

In my guidance, I simply said to follow through with management and communicate what you found. I felt this guidance was reasonable, but apparently not so. I hate to dictate to the letter exactly how to do his job. I am starting to think perhaps more handholding would be beneficial.

How can I convince him to be more assertive and not back down when challenged?


Today I had this coworker shadow me for as I and my manager had a meeting with IT management, over inconsistencies in user account provisioning. I told this coworker to observe what I said, and how I acted in the meeting. Tomorrow I plan to speaking to him about his experience.

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    Unfortunately from what you outline, I see someone who is an excellent team member but who simply is not cut out to be a leader.
    – Jane S
    Commented Mar 16, 2016 at 4:22
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    @MealyPotatoes I assume you mean "Can't"?
    – Pkarls
    Commented Mar 16, 2016 at 8:15
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    I strongly disagree with both @JaneS and MealyPotatoes. A person may be naturally meek but assertiveness and leadership are both teachable skills. I'm not sure this is the right site for a comprehensive answer about that topic but someone doesn't have to be naturally outgoing or aggressive to make a good leader.
    – Lilienthal
    Commented Mar 16, 2016 at 9:36
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    Anthony, some important questions: how much experience does this team member have, how much (if any) management experience and what is his position compared to the management people you think he should stand up to? And have you actually told him that he should be holding his ground and that it's okay for him to disagree with them and escalate to you if that causes problems? Finally, are you a mentor or a manager of this person? If you can't protect him from fall-out then you're doing him a disservice by telling him to stand up to upper management.
    – Lilienthal
    Commented Mar 16, 2016 at 9:39
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    @Lilienthal, auditors by definition have to stand up to senior management.
    – HLGEM
    Commented Mar 16, 2016 at 16:02

5 Answers 5


This is a critical job skill for an auditor. It is an auditor's job to find things that management is not happy about. The sole reason for auditing is to put an outside set of eyes on processes, procedures and finances in order to prevent fraud, inefficient operations, security issues, etc. Those are not things managers want highlighted, so, by nature, auditing is an adversarial function. You must have a thick skin and an ability to not back down when you are right as well as an ability to be able to add in additional information that might mitigate your findings.

You can train some of this, but it is possible that some people cannot become assertive enough to succeed in the profession.

First thing to do is to get him to understand that it is his job to find things that will upset management. He needs to understand that his boss will be upset with him for backing down when he was in the right. He needs to understand that his boss will stand up for his findings.

There is close to a 100% chance managment will push back on findings in an audit report. When I worked for Navy Audit, we had push back on all reports. Auditors have to learn to stand firm. If he starts giving in all the time, he will not have the skill to really hold firm on a critical item. He must know that this is a make or break skill for this profession.

What we did to train people in this skill was:

First no junior person was ever the one who did the final response to management. He should not be the one who provides the final answer to their objections. This takes some of the pressure off as he learns this skill. He listens to their objections if they make them in person and should be directed to promise nothing at that point. If pressed, he is to say, "I will discuss those points with my managers and we will let you know what we decide."

He should however evaluate all objections and draft a response agreeing or disagreeing. Then you, as the senior person, should look at the objections and his draft response and correct it when it is giving in when it should not be. Don't rewrite the response though, give it back to him with your criticisms and make him rewrite it until it is acceptable to you. He needs to know that giving in is not acceptable performance unless management provides some information that the auditor did not have or unless he has made a serious mistake (hopefully his (and everyone else's) work was reviewed by a quality control before being sent to management for comment so you won't have that issue.) Once you have the written response under control and he knows what is expected, you can move on to the presentations (if you do actual oral presentations).

Then you start small in letting him learn to present the responses back to management. Take a fairly easy issue, that is not controversial and have him to do the actual presentation and stand firm. Do not move him up to more complex issues until he can stand firm through the less controversial. It may take 2-3 years to train him up to the level of a senior auditor who can stand up to management on anything.

If you explain to him that standing up for his findings is part of his job and he continues to give in over time and you see no improvement, then he needs to be put on a Performance Improvement plan and if he still can't improve, he needs to be removed from auditing. This is a critical skill, you can't afford to keep someone who can't develop it.

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    +1 also on the critical requirement of an auditor. If he doesn't learn this, he needs to know that giving in to management, if something goes wrong, will ALL go back to him. He will be in serious trouble if an audit reveals critical flaws, but the report was recanted without acceptable reason.
    – Nelson
    Commented Mar 17, 2016 at 3:06

Honourable mention to WorkerWithoutACause's answer. He covers many other points I am not covering.

I will give you an answer based on methods:

It appears that the person concerned is potentially lacking in a few common areas that are often very often not taught behaviours in early life. The skills you are expressing a need for from him are definitely "soft skills" and can be taught but they need to be encouraged and brought out through example and formalising (to a extent) your interactions with him. "Getting what you want" is one of the soft skill dark arts.

  • Lead by Example: Have you offered him the opportunity to observe someone fighting management and getting their way? Has he observed you doing this? To learn the behaviours you need from him you must expose him to how you want him to act/react in the situations where he is falling short. Get him into a meeting where you have to fight your corner to management (obviously with the permissions of people in the meeting) he could be taking minutes for you or supporting you technically. Once the meeting is over, ask to have a 1-2-1 with him so you can discuss how you acted in the meeting and what you specifically did in reaction to the comments made by management.
  • Targeted improvement: Is this need to be more assertive part of his personal development plan? It should be! often managers shy away from setting personal soft skill targets to their team members for fear of offending, but displaying a genuine interest in improving someone is usually met with positive discourse. However, it needs to be wrapped up as a opportunity to extend his soft skills, not fill a gap in his soft skills.
  • Create a method "I simply said to follow through with management and communicate what you found." This is only the first step in persuading, Shell and Moussa [1] explain that there are 4 steps:

    • Survey the Situation: what are his own situation, goals, and challenges he may face in persuading.
    • Confront the 5 barriers: Relationships, credibility, communication mismatches, belief systems and interest. He should look at how the people he is persuading are influenced by these and look to adapt his argument to persuade them.
    • Make the pitch: Using a solid justification based in reason and good presentation skills to engage and explain.
    • Secure commitments: He must make sure that the people he has persuaded are fully invested and make solid commitments that are followed up on.

    This is not to say that this is the only method for persuading, there are numerous methods that can be grouped into using reason (logic/scientific), emotion (faith/imagination/tradition), body language and other (not recommended) less ethical methods.

Another good read on understanding influence is Robert Cialdini's book on persuasion, defined six "influence cues or weapons of influence" [2]

[1] (The art of Woo by G. Richard Shell and Mario Moussa, New York 2007, ISBN 978-1-59184-176-0)

[2] Cialdini, R. B. (2001). Influence: Science and practice (4th ed.). Boston: Allyn & Bacon.


I've been in a similar situation to the employee you mentor. This is the outline of the improvement plan my manager and I went through:

  1. Body language: adopting positive, assertive body language actually makes you feel more positive and assertive. You might want to work on improving the employee's eye contact, posture or even what they wear (the old phrase of "you look good, you feel good" applies)
  2. Multiple solutions are OK: I've found that some people who are conflict-averse hold the believe that most problems have one best answer. This is frequently not the case. There are multiple ways to solve a problem and they can be combined. You may want to mentor the employee to think of these conflict situations in a more creative way, such as seeing them as being mini-brainstorming sessions. It's more enticing to think of them as being a chance to be creative as opposed to being a point of conflict
  3. Learn to see questions as being solely requests for information: often 'why' questions are seen as an accusation. If you can coach the employee to see questions as being solely for information, then the employee can respond in a purely objective way, which seems to be within their comfort zone
  4. Understand the cultural background of the employee: keep in mind that people are raised differently, and that may create a clash with the company culture. I for one was taught that interrupting was very rude, but in this workplace, it was the norm. Being unable to interrupt in that workplace culture meant having no voice at all. Understanding the point of view of the employee will allow you to help them integrate better into the workplace. In my case, it was as simple as understanding that it was perfectly OK to interrupt in that workplace, even though I would never encourage that behaviour outside of that workplace
  5. Keep an open mind that the workplace may be the problem, not the employee's behaviour: in bullet point 4 I mentioned there may be a mismatch between the company's and the employee's culture, but I would encourage you to keep an open mind and suggest ways to encourage all staff to voice their opinions in a more constructive way. For example, if meetings are manic and out of control, suggest appointing a chair to keep order and allow everyone to voice their opinions
  • One note about body language - you can do mirroring/empathetic body language while talking to someone and still be assertive if you've spent a couple minutes beforehand doing a "power pose" to change your energy. The TED talk by Anne Cuddy about power poses and how they can change your body chemistry was very interesting.
    – ColleenV
    Commented Mar 16, 2016 at 17:48

It sounds like you have given valuable feedback, but the feedback itself may not have been direct enough. Radical Candor is a great way to help people develop, and focuses on offering guidance that is taken seriously (see article here: http://firstround.com/review/radical-candor-the-surprising-secret-to-being-a-good-boss/).

The idea is that there are 4 quadrants in how we interact with people ; challenging directly vs. indirectly, and caring personally vs. not caring. Where is the sweet spot? You want to challenge people directly, while giving them the sense that you are invested in them.

If you view this individual as your potential successor they are hopefully aware that you value them and are invested in their success. If not, let them know you are, this will allow your feedback to carry more weight. Next when you give your feedback, offer some candor. Not just "the what" but include the "why" (risk introduced to project, inability to advance), "appearance" (look weak) and "consequence" (won't be your successor) on failure to follow through.


How can I convince him to be more assertive and back down when challenged?

You can't, and it's not your job to. He will either grow in self-confidence as he progresses or he won't, at a fundamental level it's up to him. And usually it grows with experience and responsibility.

Engaging in conflict is assuming responsibility, a lot of people are reluctant to do so if they don't have the authority to back themselves with.

A good manager will make sure this guys work is taken seriously, he shouldn't have to argue himself.

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    A good manager will make sure this guys work is taken seriously, he shouldn't have to argue himself. Not strictly true. If this person is taking a more senior role, then he needs to have conviction that he is right. Or more bluntly, he needs to back himself.
    – Jane S
    Commented Mar 16, 2016 at 8:50
  • yep, but he's not in a senior role at the moment. Once he has the responsibility and authority that comes with it is a whole other story. Seen it happen again and again.
    – Kilisi
    Commented Mar 16, 2016 at 9:22
  • we must have different interpretations of mentor.... where I have worked it's just about teaching them the job and helping improve their tech skills, not psychoanalysing them so much and doing therapy... self confidence comes with experience and responsibility
    – Kilisi
    Commented Mar 16, 2016 at 12:19
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    If he is mentoring an auditor, this is a critical skill just like knowing a particular programming language would be for a developer. Auditors cannot afford to be meek and this is something he must help this person overcome if he is to remain in the profession.
    – HLGEM
    Commented Mar 16, 2016 at 13:35
  • good point, I didn't think of that angle. If he's not asserting himself, then he's not doing his job. Will delete my answer as soon as it reaches 50 downvotes
    – Kilisi
    Commented Mar 16, 2016 at 19:28

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