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5 Questions Leaders Should Be Asking All the Time to Support and Challenge Their Colleagues



Your answers to these 5 questions represent the work of a lifetime, so return to them regularly. The greater clarity you have about yourself, the greater your ability to lead others by example. And by continually doing the hard work of bringing your unique self to life, you give people around you a profound gift: inspiration to do the same.


Legal and compliance leaders should first focus on understanding what their organization must do. Government requirements are changing very rapidly, and some public health agencies will require citizens to get a vaccine, taking the decision out of the hands of the executive team. Consequently, it is critical that companies maintain a current understanding of the regulatory requirements in the jurisdictions in which they operate. Be prepared for the possibility that different offices and facilities may have different requirements.




5 Questions Leaders Should Be Asking All the Time




Many questions remain about the timeline and availability of the COVID-19 vaccine, making for confusing times. Several countries locked in options for vaccine supplies during the development period. But in many cases supply is not nearly enough at present to vaccinate all frontline workers, let alone other high risk groups and those in essential businesses.


While these questions are especially pertinent in the present moment, they should always guide us as we work for positive change in education. We believe we can get much better results if we pay greater attention to addressing these issues.


This gathering storm has inspired me over the past three years to seek advice from some of the top leaders in our profession and, in the process, develop a routine of considering key questions regarding the future I'm charged with leading.


Another time, we assumed that if we trained our performance advisers to give better feedback, we could develop leaders faster. When we tested this assumption, we found it was more impactful to train every team member on how to receive feedback, which transformed our leadership development and also made our performance advisers better at giving feedback.


Look, I get it. Thinking of new and effective questions to ask in team meetings can be time consuming and draining, especially on top of your never ending to-do list. So, here are two ways you can come up with great meeting questions before your next team sync:


Some time ago, Michael Smith called and asked if he could interview me. At the time, Michael was on the staff of ClearView Baptist Church in Franklin, Tennessee. We follow each other on Twitter, but we have only met one time previously. He said that he wanted to interview me on the topic of leadership. I happily agreed.


What really impressed me was how thoroughly prepared he was. Michael asked great, thoughtful questions. In fact, the questions were so good that I asked him for permission to post them here. I have printed this list out and put it in my Moleskine notebook. The next time I am with a leader I respect, I can pop out this list and start interviewing.


The technology that IT leaders choose to invest in should enable thoughtful support, intelligent selling, and engagement that your customers expect. Gauging the success of that technology will involve looking at ROI and the level detail provided in the CX metrics, and how that data can be shared within the company.


The most effective leaders are those who ask good questions. To do this, they develop great diagnostic abilities and thus can cut through seemingly complicated situations and identify the levers that will really make a difference. They have insatiable curiosity, the humility to know they can and must learn every day, and an awareness of their own limitations.


Leaders know they need the right information to make the right decisions. The only way to get the information needed is by asking for it. Thoughtful questions open lines of communication with our teams, our organizations and, perhaps most importantly, ourselves.


So, what are the types of questions leaders should ask? A good place to start are the ones management pioneer Peter Drucker posed The 5 Most Important Questions You Will Ever Ask About Your Organization:


Leaders also need to make time regularly to reflect, asking themselves questions to increase their own self-awareness, and asking their direct reports questions to build understanding, value alignment, and engagement. These questions work best when they are simple and powerful. Asking powerful questions is a critical part of how to coach your people.


Even though the questions were developed for superintendents to ask principals, I think that they should be questions any educator, parent, and even student should be able to openly ask their principal.


2. What are some areas of teaching and learning that you can lead in the school? (Instructional Leadership) Covey talks about two important areas for leaders; character and credibility. Many principals are great with people, yet really do not understand the art and science of teaching, or have lost touch with what it is like to be in the classroom. Although a leaders does not need to be the master of all, they should be able to still be able to walk into a classroom and teach kids. They should also definitely be able to lead the staff in workshops that focus directly on teaching and learning. If teachers understand that a principal understands teaching and learning, any initiatives are more likely to be seen as credible in their eyes.


Why you should ask your team this questionIt will give employees confidence to speak up and offer proactive advice.It shows you are committed to being open and self critical for their benefit.By listening to these answers, you\u2019ll keep growing as a manager.Follow up questionsIf you all could design the perfect manager, what are some of their characteristics?If you were managers, how would you do things differently?Pro tip: It can be intimidating to ask your team these types of questions. It puts you in a vulnerable place, but this is an essential leadership quality. Approach this with an open mind and a willingness to grow as a manager, and you\u2019re sure to get some valuable insights."}]},"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity1","name":"2. What can we do to improve our product (or process)?2. What can we do to improve our product (or process)?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity1_acceptedAnswer_Answer","text":"Why you should ask your team this question21% of employees report that if they had a game-changing idea for their organization, they wouldn\u2019t feel comfortable to share it (Officevibe Pulse Survey app data).The team will feel empowered to explore their creative ideas, and motivated to pursue them.It\u2019ll reinforce the bond between the team\u2019s efforts and the company\u2019s success.Follow up questionsWhich of our current processes is the most in need of an update? Are there any of our processes that should be retired?Are there any totally new and wild ideas any of you have for new products? I\u2019d love to hear them.Pro tip: When you hear an amazing idea, let your team member know what you think. Share it with the right people or connect the employee with them directly, and always give credit where credit is due."],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity2","name":"3. What can we do to improve our team culture?3. What can we do to improve our team culture?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity2_acceptedAnswer_Answer","text":"Why you should ask your team this questionIt shows that work is about more than accomplishing tasks.You\u2019ll boost employee engagement and show people you care.It could surface any issues that may be distracting your team.Follow up questionsHow important is company culture for everyone when it comes to doing their jobs?What would be your ideal work culture? What do you think is blocking us from that?"],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity3","name":"4. What team building activities can we do together?4. What team building activities can we do together?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity3_acceptedAnswer_Answer","text":"Why you should ask your team this questionStronger teams mean better teamwork, which results in superior outcomes.The more employees know about one another, the more they\u2019ll be able to help each other do better work.Helps build up connections on remote or distributed teams.Follow up questionsHow much time can we dedicate per month to team bonding and maintaining human connections?Do we want to schedule a recurring time slot for team building exercises?Pro tip: The success of team building activities can rely on external factors, like whether you work on-site or remotely. Take the reality of your team into consideration when you\u2019re planning these types of events."],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity4","name":"5. What (or who) is missing from our team?5. What (or who) is missing from our team?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity4_acceptedAnswer_Answer","text":"Why you should ask your team this question26% of employees say they don\u2019t have access to non-material resources such as training, support, or data, that they need to do their work properly (Officevibe Pulse Survey data).It will help guide you as a manager both with recruitment and team development.Solutions could be simple, but employees might not bring things up if you don\u2019t ask.Follow up questionsWhat is the level of urgency associated with these skills or resource gaps?How might we fill in these gaps with the resources we currently have available?"],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity5","name":"6. What else can I do to better manage our team?6. What else can I do to better manage our team?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity5_acceptedAnswer_Answer","text":"Why you should ask your team this questionIt helps you spot things you might not have otherwise noticed.It will make sure people have what they need to work effectively.Employees will feel more connected to decision-making and strategic direction.Follow up questionsDoes anyone want to pitch in on further developing and\/or implementing some of these ideas?Are there opportunities for collective leadership from the team to fulfill some of these needs?The individual employee-manager relationship is special. Asking questions in one-on-ones helps you get a monthly checkup on how people are doing. This is a great way to show you care about their personal progress, and be empathetic to hearing about their challenges."],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity6","name":"1. What\u2019s one thing you did recently you are proud of?1. What\u2019s one thing you did recently you are proud of?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity6_acceptedAnswer_Answer","text":"Why you should ask your employees this questionIt\u2019s an opportunity to see a trajectory of their progress.It will motivate employees to keep striving forward.It builds pride and confidence in the employee.You\u2019ll get added insight into what they find important.Follow up questionsDid you expect to be so proud of how your work came out? If not, isn\u2019t it amazing to surprise yourself?What\u2019s something you\u2019ve learned from this achievement that you see yourself applying going forward?Pro tip: Giving meaningful employee recognition is an essential part of management that too often gets forgotten. The answers you get to this question help you learn more about what\u2019s important to people, so you can give recognition where it will mean the most."],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity7","name":"2. What were your biggest challenges this month?2. What were your biggest challenges this month?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity7_acceptedAnswer_Answer","text":"Why you should ask your employees this question1 in 4 employees don\u2019t feel their manager is aware of their pain points (Officevibe Pulse Survey data).It can show them areas where they can focus on improving their skills.It gives you a better idea of what types of work challenge them.Follow up questionsWhat\u2019s your biggest learning from facing this challenge?How might we catch these obstacles together in advance?Pro tip: Challenges aren\u2019t always easy to articulate in person, but an anonymous feedback platform like Officevibe can help employees voice their challenges more comfortably."],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity8","name":"3. What\u2019s one thing that, looking back, you would have done differently?3. What\u2019s one thing that, looking back, you would have done differently?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity8_acceptedAnswer_Answer","text":"Why you should ask your employees this questionIt gives employees the opportunity for self-reflection and being accountable.It helps them create a roadmap to avoid mistakes going forward.They\u2019ll be more confident to try doing things differently and experimenting.Follow up questionsAt what point did you realize you should have done things differently? Was there anything you could have done to help you react faster?Was there any reason you didn\u2019t speak up at the time? I\u2019m always eager to hear your concerns, even if that means work needs to be put on pause.Is there any ongoing work that you feel might also be off track?"],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity9","name":"4. What can I do to make next month more successful for you?4. What can I do to make next month more successful for you?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity9_acceptedAnswer_Answer","text":"Why you should ask your employees this questionIt teaches people to plan ahead and anticipate where they might need a hand.It shows them that they can ask you for whatever guidance they need.Employees will get more of the support and resources they need going forward.Follow up questionsShould we set goals for you, or plan action items related to this?How will we know we\u2019ve accomplished what we set out to do?"],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity10","name":"5. Are there projects that you want to be involved in?5. Are there projects that you want to be involved in?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity10_acceptedAnswer_Answer","text":"Why you should ask your employees this question1 in 3 employees don\u2019t feel appropriately involved in decisions that affect their work (Officevibe Pulse Survey data).Employee autonomy helps people feel a deeper connection to their work.Involving employees in decision-making lets them know you value their opinion, and care about their development.Follow up questionsI didn\u2019t realize you wanted to be involved here. How do you see yourself contributing to the project?It might be too late for this one, but can we be more proactive to find similar opportunities for you coming up?Pro tip: You won\u2019t always be able to get everyone working on all the initiatives they\u2019d like to. But showing that you\u2019d like to try will help people speak up when they see opportunities they want to pursue. The more this happens, the more everyone will find their place."],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity11","name":"6. Are there projects that you\u2019d rather not be involved in?6. Are there projects that you\u2019d rather not be involved in?","acceptedAnswer":["@type":"Answer","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity11_acceptedAnswer_Answer","text":"Why you should ask your employees this questionYou open up a space where they can freely express any areas they\u2019re feeling disengaged.It\u2019ll keep job satisfaction high by preventing people from getting stuck with too many tasks they don\u2019t like.It lets the employee know they are free to express themselves, and it\u2019s safe to do so.Follow up questionsI\u2019m glad you shared this. Is there anything I can do to help you find your place on this project?Was there something I missed when I thought you\u2019d be a good fit here?How can we get you working on initiatives that are more suited to your strengths going forward?When asking your team or individual employees questions, remember, it doesn\u2019t stop with their immediate answers. You\u2019ll always want to take notes and follow up. When you follow through on the employee feedback you get, it shows you\u2019re committed to creating the conditions for great work."],"@type":"Question","@id":"https:\/\/officevibe.com\/blog\/questions-to-ask-your-team-every-month#QuestionsubjectOf_FAQPage_mainEntity12","name":"Too busy? 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