It’s five answers to five questions. Here we go…

1. My boss doesn’t trust the employee I just hired

I am a manager at a large company, and I hired an engineer under 90 days ago for a technical role, Lily. My boss, Ryan, is a senior VP and has been hands-on since he has been here since the company was small. Despite having 30+ under him, he still regularly checks out small details in new engineer’s work.

Ryan asked me to have Lily check out a new tool and give him an assessment on if it is a good fit for us. She interpreted this as “check out the documentation and compare it to competitors.” Ryan actually wanted a full-blown download, live test against other solutions assessment. A week went by and Ryan saw Lily hadn’t downloaded the tool, and wasn’t happy. Lily and I were able to download and scramble to do a quick pass. Ryan said it was a poor assessment and ended up building his own assessment.

Everyone here in my opinion made a mistake (me included), and I had a clear retrospective talk with Lily afterwards. My issue now is that Ryan has a history about it. He’s asked to have Lily and me read out reports of work she did in a private meeting and doesn’t like it when she’s tasked to do his projects despite otherwise doing her work on time and well. She’s a little resentful, he’s got a very particular picture of her, and I’m pulling my hair out as a person in the middle who is trying to manage both up and down.

I can’t change his opinion of her, or her of him, but I do need to be able to assign her work without a rehash of a now old battle. What are some scripts that I can have to say to Ryan, “I understand the history, but I need the work to be completed” and to Lily, “Yes, but he is a SVP and we need to do work assigned to us to meet business demands”?

Sit down with Ryan and address it directly. Tell him you know that Lily had a rocky start with him and that it was partially your fault for misunderstanding what he was looking for, but that she’s done good work since then and you’re worried that the early history is getting in the way of him trusting her work now. Explicitly ask for a clean slate and the opportunity to demonstrate her reliability.

With Lily, be honest that they got off to a rocky start and say that you’re committed to advocating for her now, but that the only way to “reset” with Ryan is for him to see good work from her now. Tell her (if it’s true) that based on what you know of Ryan, she’ll be able to rebuild the relationship but they both need to mentally create a clean slate for the other.

2. We stopped giving raises for a professional credential — will my employee feel baited and switched?

I am part of the senior leadership team at a small organization. Several years ago, we hired an employee for a professional role. During the hiring process, the candidate indicated they were close to completing an educational credential and expected to obtain a professional designation shortly thereafter.

At the time, our compensation system included a significant salary increase for employees who obtained that designation. The candidate initially declined our offer because of compensation concerns. Once I explained the salary progression available upon achieving the designation, the candidate accepted the position.

Since then, the employee has been a strong contributor and has been with the organization for a number of years. However, they have not yet completed the credentialing process or obtained the designation.

Recently, the organization undertook a review of its compensation structure with external consultants. As a result, the previous salary progression tied to the designation was eliminated and replaced with a much smaller recognition payment. While there was no written promise guaranteeing future compensation, I specifically discussed the salary progression during recruitment, and I believe it was a factor in the employee’s decision to join the organization.

My concern is that the employee may view this as a bait-and-switch, even though the compensation structure was changed through a legitimate organizational review. Others in leadership feel this is simply a consequence of the revised classification system and not a significant issue.

I am looking for advice on how best to communicate this change. Should I push for grandfathering the employee in to the old system? Is there a way to approach the conversation that balances transparency, fairness, and organizational consistency?

If it had only been six months or a year, I’d be a lot more concerned about this feeling like a bait and switch — and would indeed recommend that you push for them to be legacied into the old system since they accepted the job because of that specific promise. But they’ve been there “a number of years now” without getting the credential, and apparently finding their existing compensation acceptable, and it’s reasonable that compensation policies might change after “a number of years.”

You should definitely meet with them now to explain the change, but they’ve had lots of time to get the designation and haven’t, so I don’t think you need to push for them to be legacied into the old system at this point.

3. I am my boss’s succession plan — but I want to leave

I’m working at a job that is … fine. It pays pretty well, and I got a promotion a few months ago. However, it’s not in an industry I really want to be in, and I have been casually looking for other opportunities, including within my own organization since some parts of it are closer to what I want to be doing.

However, my problem is that I have all but been told that I will take over for my boss when she retires. She’s been coordinating a large area by herself for many years, and I am her first and only direct report in all that time. She has stated that I am the “heir apparent” to her position, and that would be fine, except that she’s not retiring for at least two and a half years! I’m pretty young and feel like by that time, I’ll be somewhat locked into this department and it’ll be harder to transition out. Which is worse: to leave my boss without a “successor,” potentially derailing her retirement plans, or to stick it out and possibly end up leaving shortly after taking my boss’s position anyway? I feel bad that my office has invested in training me, and they’d be blindsided and have to start all over if I left.

I saw an internal job posting a few days ago that I’m really interested in, which is what brought all this up. Would it be wrong to apply?

No. Apply! Your boss apparently made these plans without having a real conversation with you to get your buy-in, and that’s on her. You’re allowed to make your own plans that differ from hers.

Do be prepared that she’ll probably learn about it if you apply for internal openings, and at some point you’ll need to have a conversation with her about the fact that you’re interested in other areas of the organization — but it sounds like that’s a conversation that will be good for both of you to have.

4. How can I send a cover letter when it’s too late to send a cover letter?

I’ve got an interview coming up that I got 100% through my professional network — I didn’t fill out an application or send a resume or cover letter. However, there are two roles I was referred for; I’m finding I’d like to make the case for the stretch role, and it seems like a cover letter would do the best job at explaining why I think the stretch would work out.

How do I get that same message across when I’m already way past the resume and cover letter stage? The stretch role presented itself relatively late in the process, after my initial conversation with the recruiter already happened. The hiring manager for the first job would not be my manager if I were to take the stretch role, so I might not have the chance to make my case until the third round interview, at which point it really seems too late.

The purpose of a cover letter is really to get you an interview, and normally it would be a little odd to send one at this stage. However, if you haven’t yet met with the hiring manager for the stretch role, you could send her a note now, noting that you’re in process for the position and laying out your case for why you think you’d excel at it and saying you’re looking forward to meeting her. You could even say, “Normally I’d have sent you a cover letter where I’d lay this out, but because I was referred into your process by Jane Valentine, I didn’t have the chance to write one — but I’d really like to tell you why I think it might be a great match.”

5. We’re being asked to sign something illegal

I work in sales for a national company. It is highly disorganized. Sales staff at my location and within my region were given a new sales process “SOP” document yesterday and instructed to sign it and return to the regional admin. The problem is, there are actions discussed in the document which are not even legal to do in the states our location handles. The person who drafted it similarly does not live, nor work, in the states our location services, and clearly has no familiarity with the legal requirements.

We have tried to discuss this with her when she visited the office six weeks ago, clearly to no avail. We currently also have no GM at our location. Do we go straight to HR?

Yes. Explain that you’re being asked to sign a document that includes actions that aren’t legal, that attempts to raise the issue directly haven’t worked, and ask for their help resolving it.