The 10 Uncomfortable Topics You Should Discuss with Every New Employee
Avoiding them doesn't make them go away, it just makes it harder for your new employee to succeed.
When you hire a new employee, it is a time of incredible opportunity and vulnerability — for you and your direct report. Most managers spend more than a month on average to hire an employee — and that can often balloon to several months or more for more specialized or higher-level roles. The stakes are high to integrate the new hire well and fast.
As a result, most managers focus on getting new employees oriented to do the work by connecting them with colleagues, adding them to meetings, providing access to systems and tools, and sharing more detailed information about the job. These are all very valuable parts of a well-designed onboarding process, but they are insufficient if you want to create the best conditions for your new hire to be successful.
Given the pace of today’s workplace and the stress that many employees face in their work, as a manager and leader, your job is to help them get the context they need and to set them up for seamless communication and collaboration — first, between the two of you and then with the rest of the organization. To do that, you need to have some uncomfortable and time-intensive conversations.
Let’s dive in!
1. What has Changed Since the Interview (or What Wasn’t Shared)
I can’t count the number of times an employee has complained, “I wish they had told me this in the interview process.” And while the complaint may be fair, the reality is that for some organizations that are undergoing fast change, from the time an employee starts the interview process to when they join the organization, a lot may have changed.
As the manager, you need to give your employee a clear perspective of the current landscape as they get started. If metrics have dipped, priorities have shifted, or simply what was certain 2 or 3 months ago feels uncertain now, share it. You will build trust and help give your new hire the context they need to have more valuable and direct conversations with their colleagues as they get ramped up.
ACTION:
Remind yourself of what was shared with the employee during the interview process by looking at your notes and talking to the rest of the hiring team, including the recruiter, if there was one, leading the search.
Outline what is most important to share about what has changed.
In your first or second meeting, share these details. Don’t avoid them — it’ll only make it more difficult to share later and may give the appearance that you were withholding information.
2. Align on What Good Looks Like
Hopefully, this one will feel obvious to you, but for so many managers, setting clear expectations is partially completed at best and at worst, assumed.
Rule #1 don’t ever assume someone knows what you are thinking, especially when there is a power dynamic at play.
We all wish we had employees who would speak up when they have questions, but too often, the stakes feel too high to “perform” and even seasoned professionals often feel enough insecurity to stay silent.
It’s true that many employees will achieve success or at least sufficient success to be out of hot water without a more thorough discussion, but why leave that to chance.
ACTION:
Ideally, you already know what success is before you even hire an employee, but if it isn’t clear, then absolutely take the time to clarify it and write it down before the employee starts.
When you outline success, it should include at least the following:
Who they need to influence, collaborate with, and deliver value to (internally and externally)
Metrics the employee will be responsible for driving
How others on the team should value and interact with the employee and vice versa
Processes and systems the employee should become proficient with
Your definition of success doesn’t have to be complicated, but depending upon your organization’s needs, your culture, and the role itself, it does need to cover the basics above. So be prepared to detail what is needed.
One opportunity here is to align with other managers, especially those that this individual will interact with. Find out what they value and how they have set expectations on their team so that you are calibrated and in sync.
3. Start with the End
The average employee stays at a job for 2 years or less before they move on. In addition, sadly on average 30% of employees leave their job either voluntarily or involuntarily within their first year.
Navigating the departure process is often incredibly stressful for an employee, their manager, and the remaining team. With this in mind, you want to talk about what that looks like when an employee starts. The best managers build sufficient trust so that their employees come to them when they are starting to consider a departure. Those managers support their employees and co-create transition plans that de-stress and de-risk the process.
Talking about these details may feel awkward and even initially stress-inducing, but generally, people are calmed by understanding the process instead of ruminating on the unknown.
ACTION:
Set the expectation early that this is a topic you will cover in the employee’s first 90 days. This way, when you bring it up, it won’t feel like a subtle signal and instead will be received as a standard part of the onboarding process.
Prepare your thoughts in advance.
Clearly and honestly articulate how you and the company typically handle transitions and how you’d like the employee to engage with you in the future.
Not sure how this actually works, talk with your manager or HR. You’ll be doing yourself a favor.
Lastly, don’t promise what you can’t do. The goal isn’t to make the employee feel good. You are simply trying to create trust through transparency and open discussion.
4. Align on What Bad Looks Like
This is where most managers totally drop the ball because it feels like you are dwelling on the negative before the employee even gets going. But helping employees understand what is bad should actually help them focus and feel more confident about their work vs. worrying about every detail, including those that don’t matter.
While you cannot predict everything that could go wrong, you can give the employee a sense of degrees of what will be considered a moderate to severe miss and how you expect them to respond.
The key to doing this step well is prioritizing what you share — emphasizing the most important, highest impact areas is what is most helpful and will be less overwhelming.
ACTION:
Here are the areas where you want to be super clear:
What are the highest stakes parts of their job that they need to get right above all else?
What do you expect them to do if something goes wrong in a high-priority area? Should they come to you? Or is there someone else they should go to first and attempt to resolve themselves? Do you expect them to call you, even if you’re on vacation, for example?
You can also use what you outlined in #2 about what good looks like, providing examples of how and in what ways they might miss the mark. Don’t convey that they will miss the mark — this is essential. You aren’t trying to scare your new employee. You are trying to help demystify the degrees of impact.
For less experienced employees, you’ll want to be more specific and for more senior ones, you might be able to get away with more generalizations. But overall, don’t get too broad in your definitions. Aim for clarity.
5. Set Them Up with an Insider (or 2)
Many organizations now have onboarding buddies as part of their standard process, which is great. But onboarding buddies are often suggested by HR and provided on a rotational basis. They may be helpful at answering basic questions, but they often are not able to provide the level of support required to help new employees navigate nuanced organizational dynamics.
To be fair, you might want to take on this role for them because of your particular experience and perspective. But often it helps to direct your new employee to trusted confidants and collaborators in the organization to both diversify the perspectives they can access and to relieve you of the pressure of having to be immediately responsive to all of these questions.
In addition, a strong insider relationship can mean the difference between a new employee feeling isolated and unknowing versus entering conversations with more confidence and feeling better equipped to seek out the information they need.
ACTION:
Be thoughtful about who you select and whether they have the most valuable and relevant insight into how your company and its various parts work.
Take into consideration workload and temperament as well. A stressed or more reserved employee may not be the best equipped to be available and forthcoming to a new hire.
Clarify roles and set expectations with the designated insider and your new employee on how they might engage and what is reasonable to expect. You don’t want the insider feeling they have a new direct report to manage nor do you want the new employee going to the insider for every detail.
6. Describe What Keeps You Up at Night
This one is particularly challenging. Most leaders would say that less is more in terms of sharing information with your direct reports. They are generally right.
Your job as a manager is to navigate those issues that only you can address and let your employees focus on their work. However, the best managers know how to give enough context to their employees so that they can be more strategic and anticipatory in solving challenges.
By sharing the challenges you are working through that you feel are important and relevant to your new employees, you are conveying your trust in them and providing them with the bigger picture. This is an important way to also clarify why their role and work matters, which can be deeply motivating.
ACTION:
Jot down the biggest issues and challenges you see facing your company and your team.
Then look at your outline for how you defined success for your new employee.
Put a star next to each issue that has some significant intersection with the work of your new employee — those are the ones you’ll bring up. Some issues will be universal, e.g. a new major competitor or regulatory changes that impact your products and services, but some will only impact a particular region or more narrow portion of your business.
Think about how you can frame the issue without sugarcoating it, but also not be alarmist. Stick to the facts if possible. Most importantly, tie your summary back to the new employee’s role and how their work matters.
7. Share Your Decision-Making Style
While this may not be uncomfortable to talk about, it might feel like a waste of time (“they can just watch me make decisions”) or perhaps you feel your style changes based on the context, making it too difficult and not helpful to write down because it isn’t static.
Whatever your resistance, don’t avoid this step.
When you are more intentional about your decision-making approach, you are better equipped to both improve your decision-making and help your team understand how to engage with you to get to decisions more effectively and efficiently.
ACTION:
First, it’s important that you understand your own decision-making style. Some examples can include:
Do you always need to have evidence and facts?
Do you go with your gut and intuition?
Are there people you trust unconditionally?
Do certain decisions feel more difficult (e.g. people decisions or financial decisions)?
Do you have a test-and-fail fast approach? When does that apply vs. measure twice and be more thorough?
Do you seek a lot of input before you make a decision or are you more of a command-and-control leader?
Once you are clear about some of the ways you make decisions, outline those in a rough draft. Share it with a trusted colleague or direct report to get feedback on:
Is it accurate?
Is it clear and easy to understand?
Will your new employee (and possibly others) find it useful to guide them?
Make adjustments as needed and then share and review this document with your new employee.
Commit to reviewing it at least annually and updating it as needed.
Bonus: If you haven’t yet, share it with all your direct reports and create a discussion around it where you hear feedback and suggestions.
8. Align on a Feedback Approach
Just like #4 (what bad looks like), this one might feel odd to address so early when nothing presumably has gone wrong. But that’s exactly why you should tackle it early.
Talking about how you each like to receive feedback is a lot easier when you both are relaxed and optimistic about what is ahead. When you both are not stressed, you can have a more open dialogue about what will work best.
ACTION:
Share some scenarios about when you both might have feedback to give:
Your direct report disagrees about a decision you made
They feel that you didn’t listen to them in a meeting
You are disappointed with how they collaborated on a project
You felt they weren’t prepared for a presentation
Discuss how you would each handle the situation and align on what would work best for each of you. At the end of the day, you are the manager and get the final decision-making power to determine what are the acceptable ways to engage in feedback. But by having a dialogue, you might learn something about how your new hire approaches and receives feedback. You might even learn something new that you want to try for your own approach.
Don’t leave this conversation (or multiple discussions if that is what is needed) without a clear expectation for how you both will engage. It’s not enough to simply talk about feedback. To be effective, you both have to align your expectations.
9. Discuss their Fears & Needs
Most new employees are focused on learning and getting up to speed as quickly as possible. Few will be comfortable expressing fears and needs. But often times, their fears and unexpressed needs are what will limit their success.
By sharing earlier what keeps you up at night, you’ll be modeling a level of vulnerability that is appropriate for work. This conversation is the same. This isn’t about all their deepest darkest concerns in life. This is simply what keeps them up at night about their role at the company.
Your goal isn’t to make them feel better, but rather to help them calibrate what is a reasonable fear and what isn’t worth their time.
ACTION:
Share this topic and the purpose in advance. Don’t surprise your new employee and ask them to prepare 1-2 areas they want to discuss. Make sure they know that the goal is to help you understand where they have concerns, and for you to give them guidance on how to navigate them.
Depending upon what they share, you can then either help them see the fear as not likely to happen or as something worth preparing for or doing the work to avoid.
Don’t fall into the trap of promising that nothing bad will happen. You don’t need to provide false confidence. Being honest, realistic, and focusing on relevance will build trust and help your employees the most.
10. Establish Support & Boundary Expectations
Most managers’ time is limited and yours is likely not an exception. Use the early days of onboarding to address with your new hire what you are open to doing to support them and what you expect for them to resolve on their own.
Leverage the topics that you’ve already covered to guide what you discuss. Here are a few example scenarios you can use:
A high-stakes project is at risk
They are having trouble with collaboration
A colleague is making their job difficult
They aren’t confident about meeting one of their goals
They are feeling demotivated
This is also an excellent time to discuss things like vacation expectations (not just how much time, but how they should prepare for it) and how you each prefer to be communicated with, or even revisit the topic of what to do when they are starting to explore their next career path. Not sure if it’s a topic worth covering? A good guide is to name the topic and see if you feel doubt about how they will handle or respond to the situation. When you have questions, it’s a good signal that it’s a topic worth clarifying.
You are the ultimate decision-maker on what expectations are set regardless of your mutual preferences. By having a discussion first, you’ll have more information about what matters to them and you both will be able to share why you have certain preferences. Done well, you should both walk away much more clear on how to engage with each other effectively and why.
ACTION:
Outline the scenarios you want to cover and give your new employee time (perhaps one week) to prepare scenarios they will want to discuss. Here’s a sample agenda for the discussion:
Share what the objectives are for the conversation
You’ll share one scenario and together you’ll align on:
What you prefer the employee to do
What the employee would prefer to do
What you set as the expectations given your mutual preferences
Write down what you discuss and where you land
The employee will then share a scenario and you’ll discuss the same points.
At the end of the discussion, you should have outlined the expectations for 3-4 scenarios. That may be sufficient for you and your new hire to have a general model to follow. If it isn’t, schedule more time and continue the process.
At the end, share your document and that will help guide you both going forward. As you or your direct report see updates or new scenarios to add, either of you can add it to your 1:1 agenda and augment the document.
Key Takeaways
We covered a lot of ground in today’s guide. Don’t try to address all of these at once. Pick one or two that resonate the most, and work to incorporate them into your new hire process. Investing time on these topics, particularly if you haven’t in the past will not only help new employees, but likely your existing staff as well.
Set aside time to prepare and reflect on the topic before you discuss it with your new hire.
Give your new hire a heads up before you bring up these topics. Some can be shared a day in advance while others benefit from a week or more of notice. Reducing the surprise factor will greatly increase psychological safety and increase trust.
Document what you prepare and share. This will simplify your process in the future.
Connect with HR and other leaders to see what they have found to be the most valuable topics to address with their new employees. Swap tips including what working well and what hasn’t.
Keep an open door policy so that your employee feels welcome to ask questions later on after they have had time to process the information. And given the power dynamic at play, sometimes it helps to actually “pull them through the door” by asking them how they are doing and if they want to revisit any of these topics or cover new ones.
Treat this process as important, but like all other initiatives, remember that it is a chance to practice and play, to test and learn. Don’t worry about making mistakes. You will improve it over time.
Your Turn
I’d love to hear your thoughts in the Comments section on:
Are there any uncomfortable, but important onboarding topics I missed?
What onboarding topics have you found to be the most valuable to discuss with new hires?
Onboarding is as important as the hiring process in setting up a new employee for success. Let’s not avoid the difficult topics and make it stronger!
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There is a lot of good information here Kathy. It is very relevant for me as I recently had a phone pre-interview, the panel interview, a written assignment and I have a final interview in a couple of weeks. It appears to be a lot except it's for a COO position which I'm prepared for and nervous. Your thoughtful checklist has me feeling better already.
Kathy, this is one of the most thoughtful and comprehensive onboarding frameworks I’ve seen — both in content and tone. It honors the human side of leadership while still driving toward clarity and performance. That’s a tricky balance, and you’ve nailed it.
The part that struck me most was “start with the end.” We often treat departures as betrayals instead of inevitabilities — and yet, when we build trust early, exits can become just another phase of a healthy relationship, not a crisis. Powerful.
Also, the section on aligning feedback styles before things go sideways? Gold. We preach “open communication” but rarely give people a map or language when that communication gets uncomfortable.
I’ll share this with my team and invite them to weigh in — not just for new hires but to revisit our current working agreements.
Thank you for raising the bar and doing it with empathy and practical wisdom.
Matt