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Ask Your Employees These Feedback Questions To Keep Their Key Objectives On Track

Shane Metcalf, CPO of 15Five

One of the best ways to glean insights is by listening. But great listening starts with asking great questions. Below, we share some questions to ask your team members to ensure everyone is on track and to optimize success.

Questions to Ask to Drive Success with Key Objectives

Note: We highly recommend using weekly goals and quarterly objectives as a way to drive and measure performance. This can be via the practice of OKRs (Objectives and Key Results) or any other method where the top company priorities are shared and every employee creates their own quarterly priorities to support them.

1) Is your OKR to ____________ by end of quarter on track? If not, why and what are you planning to do about it?

Objectives and Key Results are one of the most powerful performance management tools you can have in a company. But unless employees track regular progress and have frequent discussions to get support from managers, their lofty work objective is unlikely to be achieved by EOQ.

2) How have you advanced your career or personal goals this week?

We can easily get caught up in the habit of getting sh*t done. That’s not time wasted, it’s just not time optimized. Every task should fit into one of three buckets; career goal, work objective, or personal advancement. It may seem strange for a manager to support a personal goal, but those are the type of experiences that create strong work relationships and deeper levels of commitment from employees.


Do you know your personal life purpose, why you are here on the planet?

The reason I ask is because until we know the answer, even if we catch what we chase, we will never be fulfilled without knowing our deeper personal (soul) purpose.

Dov Baron, Leadership Speaker and Founder, Full Monty Leadership

3) What’s the main thing standing in the way of hitting your key objectives this quarter?

Employee performance is not just about what a person needs to get the job done, but also becoming aware of the distractions and negative conditions preventing progress. Management and leadership can help improve employee performance and remove obstacles and roadblocks (especially if the manager is the roadblock!)

4) What’s the main thing standing in the way of hitting your goals for work this week?

This is similar to the feedback question above but instead of being about longer term (quarterly) objectives, this is about short term (weekly) work goals. People can muscle through a short term obstacle, whereas the question above deals with long term issues. If the answers to this question are frequently the same every time you ask, it’s time to get creative about disrupting the negative patterns affecting employee performance and quality work product.


What are you hearing that people are afraid to talk about?

Usually, there’s a lot of gossip/chatter that goes on between teams and individuals, and I want to know the real deal. You can’t ask this question unless you’ve already established trust with your team, but if you get there, you will find out an immense amount of information – some of it could be their own individual fears or concerns or it really is the water- cooler chatter. Either way, it’s important to remember that perception is someone’s reality.

Colleen McCreary, VP of People & Culture, Vevo

5) What did you learn from your OKR score this last month?

A performance metric like the percentage of a key objective that has been completed is valuable for viewing at-a-glance progress. But more important are the learnings you gain from looking at those numbers. Ask this feedback question after the first month of any given quarter, so that employees can find the source of their progress and either duplicate fruitful efforts or try something new in the event of slow progress.

6) How can I help with one of your work goals to keep team objectives on track by end of quarter/year?

Departmental goals (or team OKRs) are vital. They are the next layer down from a company-wide objective. When directors or VPs are cognizant of the struggles of middle-managers, and they step in to help change the management strategy, the entire company benefits.

7) Any concerns about the strategic goals of the company?

Our weeks (and months and quarters) are filled with tasks. Whether those tasks are actually moving the company forward is a different matter. Employees can often prioritize the wrong tasks for a variety of reasons. With so much to do and so little time to do it, it’s imperative that everyone understands what the company is trying to achieve for the year and even the rationale behind those goals. That way, everyone can ask themselves, By doing X, what strategic goal am I serving?

The importance of feedback questions

Company leaders, especially at burgeoning businesses, often take on several different roles. Regardless of what’s typed on their business card and what key objectives they own in terms of their specific team, the knowledge and skills they possess can impact other aspects of the business.

For example, I’m officially the Vice President of Customer Success. But I’ve also had the privilege of helping to shape our work culture from the ground up by creating many of the rituals that keep us connected as a team and company. Since many of those rituals involve asking employee feedback questions,I am known to the team as, The Question Master.

Questions are not only core to the 15Five product but also core to our organizational culture. For years, every Friday during our all hands meetings, I would ask a question designed to have our globally distributed team grow closer and to enhance camaraderie and collaboration. These ranged from fun questions like, What’s your secret ‘superpower’? to poignant questions like, What’s one of the most difficult challenges you’ve had to overcome in life?

The responses often come with laughter or tears, and everyone can feel the tendrils of human connection joining together from half a world away. We set out to not just build a company, but to also build a community.

The seed of question mastery is within us all, but it must be nurtured like any other skill. I became fluent in question mastery from years of training as a facilitator and executive coach. I have learned that feedback questions are extraordinarily valuable for not only eliciting information, but for spawning deep inquiry about one’s self in the personal and professional context.

After years of serving as the Question Master on Question Fridays, I recently decided to pass the baton and have a different team member ask their own questions for a month. After their month ends, they pass it on to another and then coach that person in the ways of the Question Master. In this way, everyone is gaining confidence leading team meetings, and finding their own personal voice and style when asking questions.

Our first eBook of Employee Questions remains our most popular piece of content, proving that asking questions is an incredibly valuable skill sought after in the business world. I have assembled a follow-up eBook with over sixty new questions, along with detailed information about why they are valuable or when they should be asked:

The book is broken up into ten different chapters for managers to ask feedback questions that impact culture-building, cross-team collaboration, and employee performance. There are also questions that help employees become more successful in completing their quarterly key objectives. Below, you will find the entire third chapter of the eBook (Goals & Objectives), interspersed with a couple of Genius Questions from our favorite business leadership and HR experts.

Leave a mark with thoughtful questions

Sometimes the best questions are the simplest ones like, anything else you want to share? Everyone has their own communication style. Some folks you will constantly and delicately have to interrupt, while others you will have to be very active with in order to solicit employee feedback. That’s where the power of the prompt comes in. Ask a general, open ended question to grease the wheels of the conversation and then get more specific to gain more granular insights.

There are practically infinite questions out there, and asking them can help you as a leader to maintain visibility, strengthen relationships, and gather information to help you improve leadership skills. And who knows? With a little time and a bit of practice, you may become The Question Master.

Shane Metcalf
Shane Metcalf is cofounder and VP of Customer Success at 15Five, employee performance software that combines continuous feedback, pulse surveys, objectives (OKRs), peer recognition, and 1-on-1 meeting agendas, all in one lightweight weekly check-in. Shane has spent his professional career studying organizational and human development and the power of asking the right question.