Here is today's quick question for you...​Our plan isn’t working. What do we do now?

Ask it when you're...

1. Seeing poor response to your sales and marketing motion - You’ve set expectations. And probably thresholds or tolerances, too. The results just aren’t what they need to be. It’s time to stop, evaluate and iterate.

2. Losing key people - You thought you’d created a culture to retain your best people, but for some reason, they keep leaving. You won't know why unless you ask. (HOT TIP: If your answer is money, ask again!) And you won’t change things if you don’t change.

3. Hearing NO (or nothing) from potential investors  - Something about your pitch isn’t resonating. Getting feedback on why is often tough - but it’s always worth asking. Or at least look inwards to consider what could be going wrong and build a list of possible new approaches to experiment with.

Here is today's quick question for you...​What does good look like?

Ask it when you're...

1. Starting a new role - This is a great starting point for establishing expectations with your new people leader, peers and team members.

2. Reflecting on performance - Whether you’re reflecting on your success or that of others, starting with what good looks gives you a set of criteria to guide your thinking.

3. Setting goals  - When setting goals and objectives, it’s worth thinking about the difference between good and great and how you distinguish between them for your team.

Here is today's quick question for you...​How will we know we’re aligned?

Ask it when you're...

1. Agreeing on your plans - Groupthink and HIPPO (highest paid person’s opinion) can make it look like your team is aligned. Inviting a question about alignment can help mitigate these risks.

2. Transitioning from planning to action - You’ve created the plan, and now it’s time to make it happen. As that transition occurs, it can help to share insights on how you tend to react when you feel things are going off course.

3. Working with new people  - If you’ve never worked with someone before, it can be hard to read their signals. Curiosity is the answer to that problem. Try asking them how they typically express their commitment to a plan.

Here is today's quick question for you...​What do we expect from each other?

Ask it when you're...

1. Joining a new organisation or team  - When working together for the first time, there can be a whole range of unspoken expectations that, if not acknowledged, can become traps for the team down the track.

2. Navigating tension - If things start to feel tense in your team, sometimes that’s because your expectations of each other are not being met. Asking an open question like this can help uncover the source of the problem.

3. Establishing a new partnership  - New partnerships are exciting, and there can be a tendency to jump into the work without stopping to align on how you’d like to work together. For more insights on successful partnerships, check out Wednesday Partnership by Phil Hayes-St Clair.

Here is today's quick question for you...​What will we do when priorities are unclear?

Ask it when you're...

1. Forming a cross-functional team  - Even the best-managed cross-functional project teams can find themselves at a crossroads where the ‘right decision’ is unclear. It’s helpful to plan how to handle it before it arises.

2. Getting to know a new boss - Understanding each other’s default behaviours under stress will help build trust in your relationship.

3. Delegating significant new responsibilities  - When you have a team member stepping up into something new, making it clear how you’d like to handle confusion can reassure them and reduce stress.

Here is today's quick question for you...​What are our most important measures of success?

Ask it when you're...

1. Looking at a draft list of goals  - Many teams are optimists. They impose unrealistic expectations on themselves and others in the name of ‘stretch’, ultimately demoralising everyone. If that sounds like your team, try asking this question when you’re setting goals.

2. Attempting to refocus your team - Shiny distractions can pull your team from the most important priorities throughout the year. This question can act as a circuit breaker when loud voices are shouting from an exciting but less important vantage point.

3. Reflecting on where you could spend your time this week  - When your list is longer than the time available, anchoring back to your measures of success can keep you on track.

Here is today's quick question for you...​How do we define performance?

Ask it when you're...

1. Setting new goals or OKRs  - It can be tempting to dive into detailed specifics of individual OKRs. Try starting with ‘the big question’ of what performance means to the team, and let the answers guide you into the specifics.

2. Defining your team values and culture - Aligning what performance means in the context of your culture can be a challenging yet rewarding process. It may reveal similarities and differences in the team that you were unaware of.

3. Reviewing progress  - Before jumping into ‘how did we go?’, it is helpful to revisit ‘what did we say was important’ to set the team up for a productive discussion.

Here is today's quick question for you...​How healthy is our team?

Ask it when you're...

1. Ready to guide your team to the next level  - Patrick Lencioni, of 5 Dysfunctions of a Team fame, suggests there are 4 traits of team health - Build Trust, Master Conflict, Achieve Commitment and Embrace Accountability. How does your team measure up?

2. Checking in on your team’s well-being - this is a great prompt to open up a conversation about health and well-being across the team. It can be used in 1-1s and in group settings too.

3. Reviewing your risk register  - This question can open the door to ensuring that burnout, stress and retention of key personnel are all included in your regular risk assessments.

Quick Question: What does it mean (to us) to be a team?

Ask it when you're...

1. Introducing a new structure  - Uncertainty features in any restructure, no matter how small. New teams galvanise around shared values and principles - which emerge through understanding what it means to be a team.

2. Role modelling your desired leadership culture - Demonstrating a genuine desire to understand your team will help build a culture of openness and inclusivity.

3. Observing unhelpful behaviours  - In asking for high performance, you’re likely to see a range of behaviours in the team. Some are highly individualistic and perhaps even destructive. You can set the standard by aligning on what it means to be a team.

Quick Question: How clear is our purpose?

Ask it when you're...

1. Starting a new venture  - Purpose is your magnet to attract investors, customers and team members. It’s often the reason people join you - and the reason why they stay, even when things aren’t going so well.

2. Making decisions - Purpose forms the roots from which your company grows. It creates guardrails for your biggest and your smallest decisions.

3. Sensing confusion or tension within your team  - If your purpose isn’t precise, aspirational, credible and perceived as important, your team will find it tough to align their behaviours with the company values.

   For more information about the impact of purpose on your team’s success, check out my free ebook, Scaling Teams.

Quick Question: Why does our team exist?

Ask it when you're...

1. Kicking off a planning cycle  - It might be your 5-year strategy, an annual plan or even a quarterly update.

2. Onboarding a new team member - Give your newest recruit a head start by initiating a conversation with the entire team about what you’re all about and how they fit in.

3. Facing resistance from internal stakeholders.

Quick Question: What is your guiding theme for 2025?

Maybe it's a single word that captures your intention. Perhaps it's a phrase that keeps you focused on the things or people you care most about. Or it could even be an image that represents your vision for 2025.

For me, it’s a single word…create. I love that it is an action with tangible outcomes. I’ve got a series of projects planned that are aimed at delivering this intention, but more on that later.

If you’re having trouble coming up with a theme, try using these prompts to help:

• What will success look and feel like in 2025?

• What is the one thing you’d love to achieve in 2025?

• What are your non-negotiables for 2025?

Quick Question: How should we end the year?

This is a great litmus test for how your feelings might unconsciously impact your team.

Try to listen for:

• Distractions -  projects or tasks that won't contribute to your accomplishments for the year

• Recency - it’s easy to only think about things that happened last week or last month rather than reflecting on the whole year

• Anticipation  - the things that pop into your mind as you look forward to the end of this year and the beginning of next year.

This question helps create a sense of accomplishment and sets the scene for an enthusiastic start to the new year.

Quick Question: How should we end the year?

This is a great litmus test for how your feelings might unconsciously impact your team.

Try to listen for:

• Distractions -  projects or tasks that won't contribute to your accomplishments for the year

• Recency - it’s easy to only think about things that happened last week or last month rather than reflecting on the whole year

• Anticipation  - the things that pop into your mind as you look forward to the end of this year and the beginning of next year.

This question helps create a sense of accomplishment and sets the scene for an enthusiastic start to the new year.

Quick Question: How will we know we’ve succeeded?

It’s easy to talk about high-level success indicators - but it’s worth taking the time to listen for measurable outcomes wherever possible.

Quick Question: Who has done this before?

As leaders, we often feel the pressure to have all the answers. Seeking the perspective of experienced others can help reduce this pressure and enable us to focus on the most important questions.

This question helps us remember to leverage our networks and seek thought partnership wherever we can.

Quick Question: What am I missing?

It’s tempting to only hear ‘new things’ when listening to responses. Challenge yourself to listen to how your thoughts are echoed and built upon.

Try to listen for:

• Alternate descriptions - Notice how someone new explains the problem. Let a fresh voice give you a new perspective.

• Certainty - Seek data or opinions that seem stronger and more certain than yours.

• Unexpected emotions - If your curiosity produces an unexpected response, tread gently and offer help and kindness.

This question can help deepen your understanding of both problems and people.

Quick Question: Who should I thank?

This is a question that we often ask ourselves rather than others. When holding up that mirror, the challenge is to make sure we think of all the different angles.

Quick Question: What can we learn from...?

Whether it's the end of a project, the early days of new product design or team planning, integrating past learnings is critical.

Listen for genuine insights, consistent messages and unresolved conversations.