You can ask about company strategy, leadership priorities, career growth opportunities, team challenges, and ways to contribute more effectively. Good questions show curiosity, alignment with company goals, and a willingness to learn.
Sagrika Jain
BLOG / One-on-ones


Every sector, including HR, is rapidly adopting AI in 2024. As of early 2024, about 38% of HR leaders are actively piloting or have already implemented generative AI technologies within their operations, showing a significant increase from 19% in mid-2023. This is in line with another survey where 61% of CHROs planned to invest in AI in 2024.
Do you feel disconnected from your employees, unaware of their challenges, the projects they work on, and the innovative ideas they might have?
This lack of firsthand knowledge about your employees can lead to misaligned goals, overlooked talents, and missed opportunities for innovation. It can create a barrier between you and your team, making it harder to build trust and create a collaborative environment.
Skip level meetings are the key to bridging this gap and gaining a clear, firsthand understanding of your employees’ activities. In this guide, we will explore the concept of skip-level meetings, outline best practices for excelling in them, and provide a comprehensive list of questions to ensure productive and smooth meetings.
Let’s dive in.
Skip level meetings are special meetings where you meet with employees who are at least one level below your immediate report.
These meetings allow you to bypass the usual communication chain and hear directly from frontline employees. Skip-level meetings allow you to build connections with your employees. They help improve transparency, uncover hidden problems, and discuss their solutions.
The purpose of 1:1 skip-level meetings is to gather valuable insights to enable better leadership, analyze the company’s operations, and build a transparent communication chain.
These 1:1 meetings bridge the gap between both parties—senior leaders get to see and understand your employees’ side of the story, and employees gain invaluable expertise from your leaders.
Sometimes, upper management doesn’t see the challenges on the frontline. These meetings reduce that barrier by allowing managers to communicate with frontline employees and discuss solutions. Skip level meetings also provide a learning opportunity for both parties involved.
Daniel Nyquist, Chief Marketing Officer at Crosslist, shared the importance of employee feedback. He said, “An employee once told me they needed more clarity on project priorities so they could focus their efforts. This insight helped me better guide their manager, ultimately improving productivity and morale.”
You can spot candidates’ strengths and weaknesses in skip-level meetings and allot projects accordingly. For example, if an employee shares long-term objectives during a meeting, you can suggest projects or initiatives that they might value.
Employees also benefit from skip-level meetings as interacting with you gives them a sneak peek into the company’s long-term goals and strategies.
Skip level meetings make you more accessible to employees. You get a sneak peek into their daily lives. This fosters transparent and open communication, which builds trust and makes employees feel more confident in their work.
Sunaree, Head Of Human Resources at Cupid PR, says, “Our CEO’s willingness to listen without judgment and actionable follow-up made the team begin to open up about the obstacles they faced and the resources they needed. It helped the CEO gain key insights that led to important structural changes.”
To lead productive 1:1 skip-level meetings as a senior leader, use these best practices:
To prepare for a skip-level meeting, you can review recent performance data, project updates, and feedback from direct managers. This will help you understand the context and any potential issues.
Once you have the background knowledge, set a clear agenda for the meeting. Introduce the purpose and value of the meeting to employees in advance, emphasizing that it is an opportunity for open dialogue and constructive feedback.
Also, assure employees that their input is confidential and valued. This encourages them to speak candidly about their experiences, challenges, and suggestions for improvement.
Getting on a call with a senior leader can be intimidating for employees. That’s why it’s your responsibility to create a safe space for them to open up.
To create such an environment, Harvard Business Review recommends focusing on two key aspects: permission and safety.
When an employee opens up, you must listen to them patiently. Give them enough room and time to articulate their questions, form their ideas, and discuss them clearly.
Along with verbal communication, pay attention to non-verbal cues – crossed arms, lack of eye contact, etc. – as they can reveal whether the employee is holding back or feeling hesitant.
If you notice such cues, pause and address them directly. Such pauses show that you genuinely listen to their concerns and are willing to understand.
Ask for feedback to understand how helpful the meeting was for the employee. Here are some closing questions you can ask:
Asking for feedback helps improve future interactions. Feedback shows that you value the employee’s time and opinions and are committed to making the process as effective and beneficial as possible.
Remember to thank the employees for their honest feedback and follow up on any actionable points they raise. This will demonstrate that you’ve taken their input seriously.
To do this, you can do these meetings with Peoplebox.ai and review the most mentioned points. This will allow you to be fully attentive during the meeting instead of jumping in and out to write your thoughts down!
Clearly outline the key points you want to discuss with the executives for an insightful and enriching conversation. You can take a self-assessment test to identify your KPIs, strengths, and weaknesses.
Gauri Manglik, CEO & Co-founder of Instrumentl, shares, “Employees should come armed with 2-3 well-thought-out talking points highlighting your achievements and contributions over the past quarter or year. Quantify your impact whenever possible.”
While outlining your achievements, make them specific and quantifiable.
For instance, instead of saying, ‘I helped boost team productivity,’ say, ‘I introduced a new project management tool that increased team productivity by 25%, resulting in the on-time delivery of all projects over the past year.’
Some talking points employees can use during these meetings:
It’s natural to feel intimidated, especially when you’re going to these meetings for the first time. Thoughts like, ‘What if I ask the wrong question?’ or ‘What if I don’t know the answer to a question?’ are more common and understandable.
To overcome this, gather as much information as possible about the senior leader. By doing so, you can feel at ease and be able to lead organic conversations, which will help you make a lasting impression on senior managers.
Jon Gordon, Managing Partner and co-founder at Sheer Velocity talks about how he made a really good impression on his executive vice president. He says, “I reviewed recent talks he had given, looked at the company’s strategic plan, and studied the goals and KPIs for his division.”
Senior leaders have years of experience to share. These meetings are your gateway to tapping into those experiences.
Ethan Evans, a Retired VP at Amazon, shares how skip levels are the ultimate source of knowledge. He says, “Assuming an average manager has 6 reports, then the skip has roughly 36 times the span (budget, projects, people) you do. That means a whole different picture.”
So, pay attention and ask follow-up questions to clarify your ideas. Treat these meetings as an opportunity to learn from senior leaders’ experiences.
Peoplebox.ai helps you conduct smooth and effective 1:1 skip-level meetings without any hassle.
To schedule a meeting, either sync your calendar (it integrates with Microsoft Teams, Google Calendar, etc.) to fetch all the scheduled meetings in a single place or create 1:1 meetings in Peoplebox directly.
Once the meeting is scheduled, create a private or shared space to share meeting notes. Peoplebox.ai also suggests talking points based on the meeting’s context, making it super easy to dive into organic conversations.
Also, you can leverage an AI meeting assistant that helps you convert your meetings into actionable notes.
A good 1:1 skip-level meeting can resurface bottlenecks, address key issues, and disperse valuable insights. By preparing in advance and building a safe environment, senior leaders can connect with employees two or three levels down and gain unfiltered feedback, opinions, and ideas.
While you focus on conducting an exception skip-level meeting, Peoplebox.ai can handle all the technicalities. You just have to schedule the meeting and add the agenda and notes.
Peoplebox.ai will share talking points suggestions, convert keynotes into actionable items, and track their progress. Book a demo today to conduct your skip-level meetings!
In a skip level meeting, focus on sharing insights about your team’s progress, challenges, and ideas for improvement. Ask about company goals, leadership vision, and career growth opportunities. Be honest, professional, and solution-oriented to make a strong impression.
A skip level meeting does not necessarily mean a promotion. It is an opportunity to share feedback, discuss career growth, and align with leadership. While it can help visibility, promotions depend on performance, skills, and business needs.
Skip level meetings are usually confidential, but key insights may be shared with managers to improve processes. If discussing sensitive topics, ask if the conversation will be kept private before sharing.
To impress in a skip level meeting, be prepared, provide valuable insights, ask thoughtful questions, and demonstrate a positive attitude. Show your understanding of company goals, suggest solutions to challenges, and highlight your contributions.


How to Roll out OKRs for the first time is a question common among organizations just introducing OKRs.
Imagine a scenario-
You are rolling out OKR for the first time.
One thing goes wrong and… Boom!
Your employees are already hating the process- even before it took a pace.
You certainly wouldn’t want that to happen in your organization. OKRs can surcharge and accelerate your organizational growth. But the key is to get this done right.
That’s why a well-planned rollout is significant for the success of an OKR system.
Click Here to download ready to use OKR templates for your organization
Introduce the new goal-setting approach strategically but not in a mechanical process. Every organization is unique and can face unique challenges while implementing OKRs.
How to roll out OKRs: Here are 7 Best Practices for a successful OKR rollout
Get everyone in the organization on board with OKRs. Present the concept clearly and precisely. Educate everyone on the OKR language.
While some people will embrace the changes with open arms, there are also going to be some skeptics into the bargain. You must let them express their concerns and provide answers to their “why, how, and what?” questions.
Explain to them the benefits of implementing the OKR framework. Highlight how it’s going to impact the business and the individual success of the employees.
Organize workshops, training, discussions, introductory presentations, and seminars to help your employees’ design quality OKRs. Transparently explain to them the strategic execution, alignment, expectations, and tools they will be required to use for the purpose.
To help everyone speak the same language, document your company OKR framework
List the names of reputed companies like Google, Netflix, Intel, LinkedIn, Twitter, etc. which have successfully implemented OKRs. Narrate their success stories to help them visualize how OKRs can cater to their individual success.
For example, OKRs helped LinkedIn become a 20 Billion Company. Jeff Weiner, CEO of LinkedIn, describes OKRs as, “something you want to accomplish over a specific period of time that leans toward a stretch goal rather than a stated plan.
It’s something where you want to create greater urgency, greater mindshare.”
To read more OKR success stories, click here.
You can either go for an organization-wide rollout Consider running an OKR Pilot first, depending on what fits you best.
If you have a culture that’s open to change and a flexible structure of functioning, an organization-wide rollout will work best for you. But it’s always best to take small steps. Start from one part and gradually move to others.
Crafting and implementing OKRs across the entire organization can seem overwhelming especially if you are a large organization. Instead, choose a particular part of the organization and run a pilot project.
“If you concentrate on small, manageable steps you can cross unimaginable distances.”
It’s also important to decide “how often?” will OKRs be reviewed. Will it be done quarterly or annually?

A top-down approach to OKRs was the first pattern attempted. The top management has a significant role in setting the overall direction of the company. Starting from the top provides clarity for the rest of the organization.
“People buy into the leader before they buy into the vision.”
For example, you can start with the senior leadership team. Make them an example to roll out OKRs to the departmental heads. From there you can move on to team leaders, and to the rest of your teams.
You can’t just sit with a blank sheet in front and magically start crafting the perfect OKRs. You need to understand the context. Make the company mission and vision your starting point and tailor your OKRs accordingly.
Buy-ins are critical for OKR success. The success of OKRs depends on the collective effort of each team member. You can imagine it as a group dance performance where everyone needs to perform their parts well to make it a masterpiece.
Thus you need to align the efforts of the workforce, executive leaders, and company heads both horizontally and vertically. This will help you foster transparency, smooth cross-functional communication, and reduce overlap among departments.
Tracking OKRs are important to evaluate and measure the progress and understand which teams are falling short.
You can identify any issues and make course corrections as required by Monitoring progress.
Leverage technology to track OKRs. It will make the process transparent.
Using OKR software will also automate the calculations and save your time as you are no longer required to manually update the progress of each team member.
Bonus tip: Remember to celebrate whenever you Hit the nail on the head through OKR win meetings and shoutouts to keep
To stay on top of OKR progress, you need to do regular check-ins. Employees might feel overwhelmed with concerns and doubts, especially in the initial days.
Regular check-ins will give your employees direction. And provide them the required assistance and guidance. Frequent Check-in meetings will also identify the overlappings, increase accountability and ensure execution.
Define your preferred frequency of Check-in meetings. You can do it weekly or monthly as per your organization’s needs. Although weekly check-ins are most recommended to keep track of the progress and evaluate continuously.

Consider having OKR champion who starts implementing the OKR framework with a strong war cry. Build a team of champions who will work as ambassadors to head the change. And make the OKR framework run smoothing across the organization.
They work as mentors and internal OKR experts. And can help you adopt and execute OKRs at all levels of the organization. These OKR enthusiasts will make sure that every concern is addressed, every ‘whys and wherefores’ are explained.
Also Read: Essential Guide for OKR Champions in 2022
You might struggle when you are just starting. But after a few OKR cycles, you are sure to hit your stride.
To end, OKR’s success depends on consistency. So, remember to continuously reflect, learn, and refine the process.
Hope we were able to answer all your queries in our blog How to roll out OKRs for the first time? If you have questions feel free to comment below.

Every organization wants to grow, but how do you set goals that are both achievable and visionary? The answer lies in the types of OKRs: committed and aspirational.
Whether it’s near-term performance or long-term innovation for your business, you’ll know just how to leverage the power of committed and aspirational OKRs effectively to unlock new levels of success for your business.
Committed OKRs are about clear, attainable targets that teams can confidently deliver within a set timeframe. This type of OKR delivers accountability and is important for day-to-day business success.
Aspirational OKRs, on the other hand; push teams to be bigger and challenge themselves. The moonshots: ambitious OKRs are meant to stretch an organization from its comfort zone, kindling innovation and long-term growth.
In the rest of this blog, we will take the difference between these two types of OKR apart and see how to balance them in such a way that they enable performance as well as inspiration.
A committed OKR is a stretch goal that the team has to achieve or complete before the cycle is over. A committed goal pushes the team to reach, but still achievable attainment. All metrics of the Key Results must be completed fully and on time. Consider a situation like this:
Daniel’s organization and his teams have agreed to execute certain OKRs and have mapped a precise action plan on how they are going to do so.
These are called Committed OKRs.
An aspirational OKR sets the bar for success further out, and by design will exceed a team’s ability to execute in a given quarter. When they set such a high bar as to be seemingly impossible they are called 10x goals, or “moonshots.” While most aspirational OKRs are never fully achieved, they exist to push a team to think bigger than a committed OKR. Consider the following case:
Martha’s organization is more visionary. They have stretched goals. And her teams are not likely to fully achieve these ambitious goals.
These are called Aspirational OKRs.
Understanding the distinction between aspirational and committed goals is crucial for effective goal-setting and team motivation within the OKR framework. Aspirational goals encourage ambitious thinking and long-term vision, while committed goals focus on immediate, measurable outcomes.
Learning OKR focuses on the acquisition of knowledge, new skills, or insights rather than a direct achievement of business outputs. Extremely helpful when entering new areas or uncertainties and requires experimenting, learning, and developing new skills, Learning OKRs distinguish between usual output measuring of success and measuring acquisition of knowledge, that will later add value for future objectives. For example:
Jerry wants to gain a deep understanding of machine learning to drive full product development. He wants to finish three advanced courses and test his skills by building a model in sandbox.
These are called Learning OKRs.
When you aim for the stars, you may come up short, but still reach the moon.
– Larry Page
Read on to find out the key difference between Committed OKRs and Aspirational OKRs.
Aspirational OKRs are meant to push the boundaries and encourage employees to achieve visionary objectives. Committed OKRs, on the other hand, focus on committed objectives that offer a more realistic vision of goals with fully achievable results.
Committed OKRs help companies achieve their goals through individual and team achievements. Aspirational OKRs are often beyond the current capacities of the organization but help in pushing boundaries.
Aspirational OKRs are usually created to focus on long-term strategic vision while Committed OKRs offer short-term operational priorities to guarantee progress in the short term.
Committed OKRs are supposed to have a 100% success rate as each key result comprises fully achievable targets. Aspirational OKRs are usually found to have a success rate of 60-70%.
The difference between committed and aspirational OKRs is subtle. Committed objectives are meant to be fully achievable, requiring teams to concentrate on straightforward priorities without taking unnecessary risks, ultimately serving as motivational tools to foster small wins and consistent progress.
A standard example in the sales team scenario might be like:
Committed OKR
Aspirational OKR
In the managerial team, these OKRs can manifest like such:
Committed OKR
Aspirational OKR
In a tech context, OKRs like these can come up:
Committed OKR
Aspirational OKR
Committed OKRs will work best if your organization is newly introduced to the framework or is still in the rolling-out phase.
With each goal achieved, your team’s motivation and engagement will rise higher. In addition, teams easily get into the habit of running Committed OKRs and make it part of their work culture.
But if you have already used the framework in the past, aspirational OKRs can do wonders for you.
Creating a result-driven work culture takes time. It demands discipline, continuous effort, and a mindset shift of employees and management. So you should start simple and focus on learning the methodology first. And set up the necessary processes to make it work.
Setting aspirational OKRs in the very beginning would make your teams feel overwhelmed and over-pressurized. Extremely ambitious Key Results soon become too much to handle. Learning a new methodology takes time. Once your teams are used to the framework and it becomes a part of their work-life, you can consider aspirational OKRs.
With the later process, you can have objectives and a combination of committed and aspirational key results. While some key results will be easier to achieve, others will aim higher. Understanding the distinction between aspirational and committed goals is crucial for better goal-setting and team motivation.
Choosing the right type of OKRs depends on the organization’s goals, culture, and priorities. Committed OKRs are suitable for organizations that need to achieve specific, measurable outcomes within a set timeframe. They are ideal for teams that require a clear direction and a sense of accountability. Aspirational OKRs, on the other hand, are suitable for organizations that want to drive innovation, creativity, and excellence. They are ideal for teams that want to push the boundaries and strive for something bigger.
When choosing between Committed and Aspirational OKRs, consider the following factors:
By considering these factors, organizations can choose the right type of OKRs that align with their goals, culture, and priorities. Whether you opt for committed or aspirational OKRs, the key is to ensure that they are aligned with your company aims and internal communication processes, fostering a balanced approach to achieving both immediate and long-term objectives.
There is no one-size-fits-all answer, but where OKRs are aligned with company strategy, teams are well educated, open communication exists, and performance is reviewed regularly, it will help keep the balance between aspirational and committed OKRs intact.
However, the first step in finding equilibrium between the two forms of OKRs is that there has to be a knowledge of the difference. It needs to be apparent from the outset that everyone involved makes it clear the distinction between the two OKRs.
Teams and employees may have suitable insights that will assist in determining what is realistically achievable (committed) and what is a stretch but possible (aspirational). This can help determine what the balance ratio for the OKRs is going to be.
A very critical element to succeed with OKRs is reviewing and tracking the progress. With weekly check-ins, teams can go through their OKRs regularly and update the same performance data. It becomes easy to track how they have progressed on the outcome of the OKR in the OKR review process.
The grading of OKRs is very clear on the distinction between committed and aspirational goals. Committed OKRs are things to be accomplished within the cycle, and grading is binary: pass or fail. That is, an OKR is said to be successful if 100% of it is accomplished; otherwise, it is regarded as a failure. Aspirational OKRs, on the other hand, are graded along a more nuanced scale.
Here are 6 common mistakes organizations commit while setting up aspirational OKRs-
A common mistake most organizations commit while writing aspirational OKRs is to write something like, “What can be done more if we have extra resources and luck favors us ?” Instead, you can pretend to be a genie and strive to understand “What our customer needs at present moment?”
Aspirational OKRs don’t imply setting unrealistic goals. It should be achievable, with the understanding that your teams won’t have any clue about how to achieve these OKRs. Aspirational OKRs demand overuse of resources. They are fluid and flexible. But still helps your teams focus on well-defined goals.
Moving forward with a “Who cares?” attitude is a common pitfall among organizations. Low-value objectives go unnoticed even after the successful completion of the key results.
OKRs are a tool for organizations to work for big goals in the long run by breaking them into small chunks that can be achieved within a shorter cycle.
It makes the framework stiff and doesn’t leave scope for improvement.
How many aspirational OKRs you should set for one cycle will depend on your company’s resources. But never aim for too many Objectives and key results. As it can easily divert your focus altogether.
Implementing OKRs requires a structured approach to ensure success. Here are some best practices to consider:
By following these best practices, organizations can implement OKRs effectively and achieve their goals. Regularly reviewing and adjusting OKRs ensures that they stay aligned with the evolving needs of the organization, helping teams to maintain focus and drive continuous improvement.
Now that you know the difference between committed and aspirational OKRs and how they can impact your organization’s success, it’s the decision time. Choose the one that will best suit your purpose.
And don’t forget it’s a trial and error method. Have regular OKR check-ins and reviews. Collect feedback during and after each cycle. And use your learnings to avoid further mistakes in the next OKR cycle.


Imagine a scene! the quarter is about to end and it’s time to review and wrap up quarterly OKRs.
The clock’s ticking. Everyone is in a rush. And you are busy evaluating which goals are yet to be achieved. And what has already been done. It’s also time to think about your priorities for the next quarter.
There are so many checklists and questions going in your head.
Have my teams found ways of closing out quarterly OKRs? Will my teams beat the clock and tick all the boxes? Have they reflected on their OKR progress? How will I deal with this end-of-quarter OKRs rush?
Feeling overwhelmed!!
Here is a step by step guide to help you prepare best to wrap up your quarterly OKRs–
Click here to read champions guide for tracking OKRs
Before you start to review and wrap up quarterly OKRs- remember that wrapping up quarterly OKRs is teamwork. And to see the best results every team irrespective of their department have to come together.
Here’s the ultimate quarterly OKRs review and wrap-up checklist for you:
Track your team’s OKR progress and gather the key results scores. You can score your OKRs on a scale of 1 to 10 on the basis of how far the objectives have been achieved.
This will help you evaluate your progress in a truly data-driven manner.
Click Here to download a 15 minutes read handbook on OKRs
If the scores are low this might suggest that your OKRs were unrealistic. On the other hand, if the score is too high it may suggest that your OKRs were not ambitious enough.
Whatever learning you made from this process. It will help you to form the basis for designing your next set of quarterly OKRs.
It is important to ensure that your teams have clarity about their OKR status. At the same time, they have visibility into what other teams have been doing. It can be achieved through regular check-ins with your teams. Check this ebook on OKR handbook.
This step will help you check if your teams are aligned or not. When everyone in your team is on the same page taking decisions based on priorities becomes easy. As you have the data in hand to rely on instead of guessing.

The importance of check-ins for OKR success cannot be emphasized enough. OKR check-ins provide you an opportunity to have 1 on 1 discussion in all OKR matters.
With OKR check-ins you can discuss with your leaders and team members about – what went well, what didn’t work for them, what needs to be dealt with immediately, what problems they are facing etc. at an individual as well as team level.
OKR check-ins will help you understand what’s holding teams back. You will further get the chance to push priorities that might have shifted midway.
Organize Quarterly OKRs review meetings to dig into opportunities. During these meetings, go through each key result with your teams. Find out what went well and what needs to be done better.
Let the OKR leaders from each team present their learnings and achievements before everyone. Here teams can give a small presentation highlighting the most important lessons with context.
So that other teams can benefit from their learnings and experiences. And use them in designing their OKRs for the next quarter.
If you are a large-scale company working with multiple departments. The OKR review meetings can be held at the departmental level.
Now that you have gathered the data and matrix you need through OKR check-ins and OKR review meetings. It’s high time to plan for the next quarter.
OKRs have the power to build the future of your organization. But OKR failures can cost you a fortune.
Hence it’s important to find out the core reasons behind your OKR success or failure for the present quarter. And use it as context while designing OKRs for the next quarter.
“Should OKRs change every quarter?” is a question often left unanswered.
Even after an OKR is achieved, you can roll it forward for the next quarter if necessary.
For example, if your OKR was to increase customer satisfaction by 20% in the present quarter. This could be relevant even for the next few quarters.
In case, of missed OKRs, you need to take a call. And decide whether you want to carry it forward or set new OKRs based on the data gathered.

You should preferably wrap up the quarterly OKRs at least a week prior to the beginning of the next quarter.
But the preparation and discussions for the next quarter should be initiated almost a month before the new quarter begins. This is because designing OKRs takes dedication, time, and effort.
Bonus Tips:
Wrapping up end-of-quarter OKRs will allow you to pause and take a moment to think. It provides you time to reflect on your wins, failures, and setbacks. It’s a stitch in time to make sure that your OKR framework is a success.
Follow the steps given to close out quarterly OKRs and make the most out of the process.