Articles / Leadership Training Questions to Ask: Your Complete Guide
Development, Training & CoachingDiscover the critical leadership training questions that measure ROI, assess needs, and drive real behaviour change in your organisation.
Written by Laura Bouttell • Mon 1st December 2025
Here's a sobering statistic that should give every organisation pause: whilst companies worldwide invest over £290 billion annually in leadership development programmes, a staggering 75% of organisations rate their efforts as "not very effective." The culprit? They're asking the wrong questions—or worse, not asking any at all.
The difference between transformational leadership development and expensive box-ticking lies not in the training itself, but in the questions we ask before, during, and after the programme. When done properly, leadership training questions serve as both compass and measuring stick, guiding development whilst quantifying impact. Research demonstrates that organisations asking the right questions see an average return of £7 for every £1 invested in leadership development, with some achieving returns as high as £11. Yet only 22% of organisations actually measure the benefits of their programmes.
This comprehensive guide reveals the essential leadership training questions that separate high-impact development from corporate theatre. Whether you're designing a new programme, evaluating current initiatives, or coaching individual leaders, these questions will help you transform leadership development from a line item into a strategic advantage.
Not all questions are created equal. The distinction between a powerful leadership training question and mere administrative inquiry lies in its ability to generate insight, drive behaviour change, and create measurable outcomes.
Effective leadership training questions share four critical characteristics:
An effective question must be actionable—it should illuminate specific behaviours or decisions that can be modified. "How satisfied are you with leadership communication?" tells you little; "What specific communication behaviour would have the most impact if your leader changed it tomorrow?" creates a clear path forward.
The question must be measurable—if you cannot quantify the response or track changes over time, you cannot demonstrate impact. This is why 86% of organisations measure how learners react to training, yet only 39% measure whether participants actually apply what they've learnt. The former is easy; the latter drives results.
Great questions are psychologically safe—they invite honest reflection rather than socially desirable responses. Research from the Centre for Creative Leadership confirms that self-awareness is the hallmark of great leadership, yet too many assessment questions encourage leaders to present idealised versions of themselves rather than confront genuine development needs.
Finally, powerful questions demonstrate strategic alignment—they connect individual development to organisational objectives. When asked properly, these questions reveal not just what leaders need to learn, but why it matters to the business.
Brain imaging research reveals why certain questions catalyse development whilst others fall flat. Open-ended questions that require reflection activate the prefrontal cortex, the brain region responsible for complex thinking and self-regulation. By contrast, yes/no questions or those with obvious "correct" answers engage only surface-level processing.
As leadership development expert Niels Lameijer explains: "Awareness is the first step toward change. Being aware of one's journey and what shaped them—the good, the bad, and the ugly—is crucial for becoming a better version of themselves." This awareness emerges only when questions penetrate beyond comfortable territory into genuinely reflective space.
The pre-training phase determines whether your leadership development investment will yield dividends or disappear into the ether. Yet nearly 60% of first-time managers report receiving no training when they transition into leadership roles—a failure that begins with organisations not asking fundamental questions about readiness, needs, and context.
Before designing any leadership programme, you must understand the organisational landscape:
What specific business challenges must our leaders address in the next 12-24 months? This grounds development in reality rather than generic competency models. If your organisation faces digital transformation, questions about change leadership become paramount. If growth through acquisition is the strategy, integration and cultural alignment rise to the fore.
Which leadership behaviours currently drive—or impede—our strategic objectives? Research shows that 51% of organisations focus their leadership development on reducing employee turnover, yet this is a lagging indicator. The question should identify the leading indicators: which specific leadership behaviours correlate with retention in your organisation?
What has been our historical approach to leadership development, and what were the measurable outcomes? Organisational memory matters. Understanding past successes and failures prevents reinventing wheels or repeating mistakes. More importantly, it establishes baseline metrics for comparison.
How does our organisational culture support or undermine leadership development? A question rarely asked but critically important. The most brilliant training programme cannot overcome a culture that punishes vulnerability, discourages experimentation, or fails to reward new behaviours.
Moving from organisational to individual level, these questions identify specific development requirements:
For Emerging Leaders:
For Mid-Level Leaders:
For Senior Executives:
These tiered questions recognise a fundamental truth: training needs vary dramatically by career level. Entry-level leaders need foundational skills; mid-level leaders require the ability to lead through others; senior executives must master strategy, change leadership, and organisational politics.
The heart of effective needs assessment lies in identifying the gap between current and required performance:
What is the difference between your current leadership capabilities and those required to achieve your objectives? This question, deceptively simple, forces clarity about both present state and desired future.
Which knowledge, skills, and abilities would have the greatest impact on your effectiveness if developed? The Pareto principle applies to leadership development: 20% of capabilities drive 80% of results. This question helps identify that critical 20%.
What environmental factors or organisational barriers might prevent you from applying new leadership skills? A question that acknowledges reality: training is necessary but insufficient. If the organisation does not support new behaviours, they will not persist.
How will you measure whether your leadership capabilities have improved? Self-defined success metrics create ownership and provide baseline for assessment. Leaders who can articulate their own measures of progress are far more likely to achieve meaningful development.
If pre-training questions establish the foundation, evaluation questions determine whether you've built anything substantial upon it. The challenge is that most organisations measure the wrong things.
Research reveals a troubling pattern: whilst 86% of organisations measure learner satisfaction with training, only 39% measure application of learning, and merely 22% measure business benefits. This is rather like judging a restaurant solely by how pleasant the dining room is whilst ignoring whether the food is actually edible.
The classic Kirkpatrick Four-Level Training Evaluation Model remains useful, but requires sharper questions:
Level 1 - Reaction Questions: Rather than "Did you enjoy the training?" ask:
Level 2 - Learning Questions: Move beyond knowledge tests to application:
Level 3 - Behaviour Questions: The most critical yet most neglected level:
Research indicates that 78% of HR leaders consider behaviour change the most valuable measure of success, yet many struggle to track it. The solution lies in 360-degree assessments conducted before training and 60-90 days afterwards, revealing actual behavioural shifts rather than self-reported intentions.
Level 4 - Results Questions: Connect development to business outcomes:
To justify continued investment, you must answer the financial question directly:
The fundamental ROI question: "For every pound invested in leadership development, how many pounds of value have we created?"
To answer this, you need baseline measurements:
Then measure these same metrics 2-6 months post-training. The comparison reveals whether your £1 investment returned £3, £7, or £11—or nothing at all.
One particularly effective approach: compare teams led by trained leaders against those led by untrained leaders. This quasi-experimental design controls for organisational variables and isolates the impact of leadership development.
Leadership development is not an event but a continuous process. The questions that sustain growth differ from those that initiate it.
Drawing on established coaching frameworks like GROW (Goal, Reality, Options, Will), these questions foster ongoing development:
Goal-Focused Questions:
Reality-Assessment Questions:
Options-Exploration Questions:
Will-and-Action Questions:
Research from Gallup demonstrates that leadership quality impacts employee engagement by 70%, yet this influence depends on sustained behaviour change, not one-time training. These coaching questions, asked regularly, maintain the developmental momentum.
The most powerful leadership development is self-directed. These questions facilitate the reflection that drives continuous improvement:
Weekly Reflection:
Monthly Assessment:
Quarterly Evaluation:
As Jim Knight notes in The Definitive Guide to Instructional Coaching: "Questions are to coaches what ice skating is to hockey players: if you want to play the game, you have to learn the skill." The same principle applies to leaders: asking yourself the right questions is fundamental to growth.
Thus far, we've focused on questions asked about leaders. But the most powerful development often comes from questions leaders ask of their teams.
Research shows that employees are 3.5 times more likely to leave within a year if they perceive poor interpersonal skills in their leadership. The antidote? Leaders who genuinely seek feedback and act upon it.
These questions invite honest feedback whilst maintaining psychological safety:
About Leadership Style:
About Team Dynamics:
About Organisational Connection:
The key to these questions is what happens next. Employees who see their feedback ignored or, worse, punished, will never offer honest input again. Leaders must demonstrate that feedback leads to visible action.
Beyond seeking feedback, great leaders use questions to develop their teams:
For Problem-Solving:
For Growth:
For Innovation:
These questions reflect a fundamental shift in leadership philosophy: from providing answers to asking questions that enable others to find their own answers. Research consistently demonstrates that leaders who coach rather than command develop more capable, engaged, and resilient teams.
Bringing together all the elements we've explored, here is a structured framework for comprehensive leadership training evaluation that ensures nothing falls through the cracks.
| Evaluation Area | Key Questions | Data Sources | Success Metrics |
|---|---|---|---|
| Organisational Needs | What business challenges require leadership intervention? | Strategic plans, business metrics, executive interviews | Alignment between development and strategy |
| Individual Needs | What capability gaps exist at each leadership level? | 360 assessments, performance reviews, self-assessments | Identified development priorities by role |
| Baseline Performance | What is current team performance under existing leadership? | Engagement surveys, productivity data, retention rates | Pre-training benchmarks established |
| Environmental Factors | What organisational factors support or impede development? | Culture surveys, policy reviews, stakeholder interviews | Barriers identified and mitigation planned |
| Evaluation Area | Key Questions | Data Sources | Success Metrics |
|---|---|---|---|
| Engagement | Are participants actively engaged in learning? | Facilitator observation, participation rates, in-session assessments | High participation, thoughtful contributions |
| Comprehension | Do participants understand core concepts? | Knowledge checks, case study analysis, peer teaching | Demonstrated understanding of material |
| Relevance | Do participants see applicability to their context? | Reflection exercises, action planning sessions | Specific application plans developed |
| Barriers | What obstacles to application are emerging? | Group discussions, individual check-ins | Barriers identified and addressed |
| Evaluation Area | Key Questions | Timing | Data Sources | Success Metrics |
|---|---|---|---|---|
| Immediate Reaction | What is initial response to training? | End of programme | Exit surveys, verbal feedback | Positive reception, clear action plans |
| Knowledge Retention | Do participants retain key concepts? | 30 days post | Follow-up assessments, application examples | 80%+ retention of core concepts |
| Behaviour Change | Have leadership behaviours actually changed? | 60-90 days post | 360 assessments, team surveys, observation | Measurable shift in target behaviours |
| Team Impact | How has team performance changed? | 90-180 days post | Engagement scores, productivity metrics, retention | Improved team outcomes |
| Business Results | What business impact has occurred? | 6-12 months post | Financial metrics, strategic progress, comparative analysis | Positive ROI, strategic advancement |
This structured approach addresses the reality that only 26% of organisations prioritise measuring training programme effectiveness. By building measurement into the programme design itself, evaluation becomes integral rather than afterthought.
Particularly effective is a structured follow-up schedule:
30 Days Post-Training:
60 Days Post-Training:
90 Days Post-Training:
Research shows that managers in the public sector who received executive coaching following leadership training demonstrated an 88% boost in productivity. The coaching—structured around these types of questions—transforms knowledge into sustained behaviour change.
Even well-intentioned organisations stumble when crafting leadership training questions. Avoiding these pitfalls significantly increases the likelihood of meaningful development.
"Did you enjoy the training?" is perhaps the most frequently asked and least valuable question in leadership development. Satisfaction correlates weakly with learning and even more weakly with behaviour change. Comfortable, entertaining training that leaves participants unchanged is a failure, regardless of satisfaction scores.
The fix: Ask instead about anticipated application: "What will you do differently on Monday because of this training?" This question forces participants to translate concepts into action whilst fresh in their minds.
"I need to improve my communication skills" tells you nothing actionable. What aspect of communication? In what context? Measured how?
The fix: Follow every generic answer with specific probes: "Give me an example of a communication situation you handled poorly last week. What exactly would you do differently now? How would you know if your new approach worked better?"
Training questions that focus solely on individual capability whilst ignoring organisational context set leaders up for failure. Research on behaviour change confirms that environment shapes behaviour more powerfully than knowledge or intention.
The fix: Always include questions about context: "What organisational factors might prevent you from applying these new skills? How will you navigate those barriers? What support do you need from the organisation?"
Most training evaluation stops with individual leaders, yet leadership impact manifests through teams and organisations. A leader who develops new skills but whose team performance remains unchanged has not actually developed.
The fix: Always include team-level and organisational-level metrics: "How has your team's engagement score changed? What about productivity? Retention? Innovation?"
Leadership development is a process, not an event. Single-point-in-time assessment captures a snapshot, not a trajectory.
The fix: Build longitudinal measurement into your approach. Ask the same questions pre-training, immediately post, 30 days, 60 days, and 90 days after. This reveals whether development is sustained or abandoned.
Most assessment questions invite socially desirable responses. "How important is leadership development to you?" will elicit enthusiastic affirmation regardless of actual belief.
The fix: Ask questions that surface genuine barriers and resistance: "What aspects of your current leadership approach would you prefer not to change, and why? What trendy leadership concepts do you think are nonsense? When has development training felt like a waste of your time?"
These contrarian questions reveal authentic perspectives that predictable questions miss. They also build credibility—participants realise you want truth, not performance.
What are the most important questions to ask before leadership training?
The three most critical pre-training questions are: (1) "What specific business challenges must our leaders address, and which leadership capabilities are required to meet them?"—this ensures strategic alignment; (2) "What is the gap between leaders' current capabilities and those required for success?"—this establishes baseline and identifies priorities; and (3) "What organisational factors might prevent leaders from applying new skills?"—this surfaces barriers that training alone cannot overcome. Without answers to these questions, leadership development becomes generic rather than targeted, disconnected from strategy, and unlikely to produce measurable results. Research shows that organisations asking these questions achieve significantly higher ROI from development investments.
How do you measure the effectiveness of leadership training?
Effective measurement requires four levels of evaluation: First, assess whether participants can articulate specific applications for new concepts within 24 hours of training. Second, measure actual behaviour change 60-90 days post-training using 360-degree assessments comparing pre- and post-training leadership behaviours. Third, track team-level outcomes including engagement scores, productivity metrics, and retention rates for teams led by trained leaders versus untrained leaders. Fourth, calculate business impact by comparing revenue per employee, customer satisfaction, and other key performance indicators before and after training. The crucial insight: 86% of organisations measure participant satisfaction, but only 22% measure business benefits. Focus your measurement where impact matters—on behaviour change and business results, not satisfaction scores.
What questions should I ask during leadership coaching sessions?
The most powerful coaching questions follow the GROW model framework: For Goals, ask "What does success look like for you as a leader 12 months from now?" For Reality, ask "How would your team honestly describe your current leadership effectiveness?" For Options, ask "What different approaches could you try to address this challenge?" For Will, ask "What specifically will you do differently this week?" Additionally, ask reflection questions that build self-awareness: "What patterns do you notice in situations where you struggle as a leader?" and "What assumptions might be limiting your effectiveness?" Research from the Centre for Creative Leadership confirms that self-awareness is the hallmark of great leadership, and these questions cultivate exactly that quality. The key is asking open-ended questions that require reflection rather than yes/no questions that encourage surface-level responses.
How often should leadership training be evaluated?
Leadership training should be evaluated at five distinct intervals to capture the full developmental arc: immediately post-training (reaction and initial comprehension), 30 days later (early application and barriers encountered), 60 days later (sustained behaviour change and habit formation), 90 days later (team impact and preliminary business results), and 6-12 months later (full business impact and ROI calculation). This longitudinal approach reveals whether development is sustained or abandoned over time. Research demonstrates that managers who received coaching following initial training showed an 88% boost in productivity—the structured follow-up transformed knowledge into lasting behaviour change. Single-point-in-time evaluation misses this critical sustainability question. Additionally, create a rhythm of ongoing evaluation through quarterly leadership effectiveness surveys and annual 360-degree assessments to track continuous development rather than isolated training events.
What makes a good leadership development question?
A good leadership development question possesses four essential characteristics: It must be actionable, pointing toward specific behaviours that can be modified rather than abstract concepts. It must be measurable, allowing you to track changes over time and demonstrate impact. It must be psychologically safe, inviting honest reflection rather than socially desirable responses—this means avoiding questions that have obvious "right" answers. Finally, it must demonstrate strategic alignment, connecting individual development to organisational objectives and business outcomes. For example, "How satisfied are you with your leadership?" fails these tests—it's neither specific nor measurable. By contrast, "What specific leadership behaviour, if changed, would have the greatest positive impact on your team's performance, and how would you measure that impact?" meets all four criteria. The difference between powerful and pedestrian questions determines whether development generates genuine growth or merely performance.
Should leadership training questions differ by leadership level?
Absolutely. Training needs vary dramatically by career level, and questions must reflect these distinctions. For emerging or first-time leaders, focus on foundational skills: "What aspects of managing people do you find most challenging?" and "How comfortable are you giving feedback and managing performance?" These leaders need basic leadership mechanics. For mid-level leaders, shift to leading through others: "How effectively do you delegate versus doing work yourself?" and "How equipped do you feel to manage cross-functional conflict?" These leaders must multiply their impact through others rather than personal contribution. For senior executives, focus on strategy and transformation: "Which capabilities that served you well previously may now limit your effectiveness?" and "How prepared are you to lead transformational versus incremental change?" Research confirms that what makes someone effective at one level often differs from—or even contradicts—what makes them effective at the next. Questions must evolve accordingly.
How do you calculate ROI on leadership training?
Calculate leadership training ROI using this formula: [(Monetary Benefits - Training Costs) / Training Costs] × 100. To determine monetary benefits, establish baseline measurements before training for: voluntary turnover rates and replacement costs, revenue per employee, productivity metrics, and employee engagement scores. Measure these same metrics 2-6 months post-training. For example, if annual turnover costs decrease from £500,000 to £350,000 (£150,000 benefit) and productivity improvements generate £200,000 in additional value, total benefits equal £350,000. If training cost £50,000, your ROI is [(£350,000 - £50,000) / £50,000] × 100 = 600%. Research shows leadership development yields average ROI of £7 for every £1 invested, with returns ranging from £3 to £11. A particularly effective approach: compare teams led by trained leaders against those led by untrained leaders, isolating leadership development's specific impact whilst controlling for organisational variables. Without this calculation, leadership development remains an act of faith rather than strategic investment.
The leadership training questions you ask—or fail to ask—determine whether development drives strategic advantage or merely checks compliance boxes. In an era where organisations invest nearly £300 billion annually in leadership development yet 75% rate their efforts as ineffective, the difference between success and failure lies not in training methodology but in the questions surrounding it.
The research is unequivocal: organisations that ask rigorous questions before, during, and after leadership training achieve dramatically superior results. They see the £7-to-£11 return on investment rather than negligible impact. They develop leaders who change behaviour rather than collect certificates. They create cultures of continuous development rather than episodic training events.
Yet asking good questions requires courage. It demands that we confront uncomfortable truths about current leadership effectiveness, organisational barriers to development, and whether our training investments actually produce results. It requires that we measure what matters—behaviour change and business outcomes—rather than what's easy—satisfaction scores and attendance records.
The questions outlined in this guide provide a comprehensive framework for leadership development that drives genuine impact. They span the full development lifecycle from pre-training needs assessment through post-training evaluation and ongoing coaching. They address multiple levels from individual leader to team to organisation. They balance strategic alignment with psychological safety, rigour with practicality.
But frameworks matter only when implemented. The question now is yours: What will you ask differently about leadership development in your organisation? And more importantly, what will you do with the answers?
As the management theorist Peter Drucker observed: "The important and difficult job is never to find the right answers, it is to find the right question." In leadership development, asking the right questions transforms investment into impact, potential into performance, and training into transformation.
Sources: Research.com Leadership Training Statistics; TeamStage Leadership Statistics; GetSession ROI Measurement Guide; Changing Point Training ROI Research; DDI World ROI of Leadership Development; Leapsome Leadership Survey Questions; Centre for Creative Leadership Research; Workhuman Coaching Questions Guide; AIHR Training Needs Assessment; CDC Training Needs Analysis