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30-Day Conversation Questions
May 9, 2023
Reduce risk, improve the health of your culture, and set your team up for success!
Imagine that your organization is growing, and you hire someone to join your team. You're excited! You feel like you found the exact person you've been searching for—a real gladiator, a champion—and you're alive with hope for the future.
Fast forward a few months; the bright future you imagined has been overshadowed by a dark cloud. Your champion isn't proving to be the conquering hero you thought they were. You're scheduled to have a 90-day review conversation next week, and you're not looking forward to addressing your concerns. More than that, you're afraid you may have to dismiss your gladiator if you can't figure out the problem.
I've put together a list of nine strategic questions (plus one bonus question!) that you can use to facilitate a productive conversation 30 days into a new recruit's employment. Having this conversation sooner rather than later will give you the information you need to correct behaviors before those clouds start rolling in to cast a shadow over your bright future—and theirs.
Nobody wants to be average
Do you remember those anti-drug PSAs from the 90s where kids share what they want to be when they grow up?
One in particular begins with the image of a guy running. A child's voice says, "I want to be a track star when I grow up." Just then, a policeman enters the frame to reveal that the guy is being chased by the police. Then the narrator gives this punchline:
"Nobody ever says, 'I want to be a junkie when I grow up.' Don't let drugs get in the way of your dreams."
Those commercials were short, but they delivered a powerful message.
In our worlds as leaders, a similar and equally profound truth exists. Nobody ever says, "I want to be average when I grow up." We were created in the image (physical form) and likeness (character) of God, and scripture clearly states that we are God's masterpiece and that He has created us anew in Christ Jesus, so we can do the good things he planned for us long ago. That doesn't sound average to me.
When team members underperform, it's usually because of one or more of these three issues:
- They are stuck.
- They are lacking some sort of skill or training.
- They lack clarity or security, so they're scared and underperforming out of anxiety.
The good news is that there are solutions for all of these, but first, you must address them. Don't let a lack of communication keep you or your team from thriving.
Benefits of giving feedback early and often
Even if you're 100% comfortable with confrontation, having to let someone go and start the hiring process all over again feels like a waste of time and resources that no responsible leader wants. In most cases, this scenario is avoidable. The key is to give and receive feedback early and often.
It's common practice to facilitate a 90-day review with all new employees. Some even refer to those first 90 days as "probation," understanding that in that time, either party can choose to end the business relationship. No harm, no foul.
But wouldn't it be better stewardship of your team members, and the organization, to have that conversation sooner?
A lot can happen in 90 days, so we encourage leaders to have their first conversation at the 30-day mark. In this conversation, you should explore areas where they shine and validate their success so far. You should also explore areas where they aren't meeting expectations and work together to find solutions. But it's not always about what they are doing right or wrong.
Sometimes, hidden in our policies, procedures, and culture are blind spots that require the perspective of an outsider or newcomer to expose them. Where a 90-day review is about the employee being evaluated, this 30-day conversation focuses more on the employee evaluating you and your organization. Using the questions below, you will discover ways that you and your organization can better serve your team and set them up for success.
Sample questions with details
So, exactly how should that conversation go, and what questions should you ask?
Here are 9 questions to ask in your 30-day conversation:
- What do you enjoy most about your new job?
It's crucial to begin this conversation on a positive note. Get them talking about what makes them excited. This will give you insight into where they believe they're excelling, and it's a great opportunity for you to affirm them. - What do you enjoy least about your job?
You might think there isn't much you can do with their answers to this question. After all, everyone has aspects of their role that aren't their favorite. We may even dislike them, but it's not just about what they enjoy least. Oftentimes, someone doesn't like an aspect of their job because they lack some skill, training, or resource to do it successfully. Listen to their answers, and explore ways you might be able to help them enjoy these parts more. - Are you frustrated with any aspects of your new role?
You're likely to get an initial answer somewhere along the lines of, "No, everything is fine." But you should press into this. You want them to use the same level of candor they might use in an exit interview when there's nothing to lose. You may have to narrow the focus and ask more direct questions to get them talking. (Have you been frustrated yet? Is there something you lack clarity about?) - Do you feel like you have adequate resources?
We have countless tools and resources available to help us succeed in our roles. (This blog and the PDF download at the end are both great examples!) As leaders, we depend on the members of our team to tell us which tools they need. Keep in mind, this could also highlight areas in which they need more training.
Another way to phrase this question is, "What's limiting you?" This could be things inside their circle of control or outside of it. Either way, you want to identify areas that, if improved, would foster an environment for your team to thrive. Are there any skills deficits or organizational constraints holding them back? - What do I do as your leader that makes your job harder?
This question is not for the faint of heart. A true leader asks for honest feedback and doesn't take it personally, recognizing that every leader has areas that need to grow all the time. Jump into the middle of this question with excitement! Remind your new recruit that you want them to use the same candor they would in an exit interview. - What can I do to make your job easier?
Hopefully, pressing into the previous question will make answering this one a little easier for them, but you may have to reaffirm your desire for honest and open feedback. As we say at Integrus, "Feedback is the breakfast of champions!" - When in the last 30 days have you felt led well?
Pay close attention to how they answer this question. They are telling you the best way to ensure they feel cared for. Their answers will shed light on what's important to them and what they value about the workplace culture. - Are there any relational dynamics that are challenging or compromising your work?
As long as we are working with other people, relational dynamics will always provide an opportunity for conflict. And that conflict may go unresolved for lots of reasons. So, with this question, you want to find out if they're struggling to get along with anyone and why. Then, you can use this as an opportunity to reaffirm how your team's culture dictates you deal with conflict and, if needed, provide support in facilitating healthy resolution. - What have you learned in the last 30 days that we should have shared with you during onboarding?
I love this question! As a leader who cares about the success and well-being of my team, I want to make sure that we've created an onboarding process that serves both the organization and new recruits. There will forever be ways we can improve, but if each person only goes through onboarding once, then it's imperative to get feedback from each person in their first 30 days while their experience is fresh.
CAUTION FOR LEADERS: Do not ask for feedback if you don't plan to do anything with it! Take great care to follow up with your team to let them know how you're working to address their concerns. There is no greater enemy to an organization's culture than a leader who asks for honest feedback and does nothing to make the necessary changes.
Bonus Question
I've given you my top nine questions to ask in a 30-day conversation, but there's one more that could prove to be a total game-changer for your leadership.
- How is your spouse or significant other (and family) dealing with your transition?
When starting a new job, any changes to a new recruit's routines at home can cause tension while they work out a new normal. And they will carry that tension into their day. So, if there's anything you can do to make the transition easier, do it! Not only will you set your new recruit up for success, but you will also begin to build loyalty and relational capital by showing genuine concern for their family.
You may be questioning whether bringing personal matters into the workplace is productive, or even healthy. But the truth is that if they're having a problem at home, it will bleed into their work. So, if that monster is going to show up anyway, don't wait for it to be Godzilla-sized and start wreaking havoc on your "city." Be proactive by asking this question and helping where you can.
Download the PDF
Don't wait to begin implementing a 30-day conversation and asking these questions.
Even if you don't have new recruits onboarding any time soon, you can ask your team these questions at their next regularly scheduled review. Especially if you haven't made it a practice to ask these types of questions with your team. While we encourage leaders to give and receive feedback early and often, it's never too late to start!
Our team at Integrus put these questions into a PDF that you can download and use when facilitating your 30-day conversations. Download the PDF, take notes on it, and then use the information you gather to make improvements for your team. You will find that by tending to the needs of the individual, you will simultaneously extend the longevity of your team members and strengthen your organization's culture!
Downloading is easy.
- Click the "Download" button.
- Enter your name and email.
- Check your email for your download.
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