Let Your Team Struggle In Order For Them To Grow

In theory, most leaders know how important it is to delegate challenging tasks to employees both to help them grow and create a collaborative, empowered, productive team. But, faced with real workplace demands, it can be tough to put this into practice. Many of my clients say things like “I’m the only one who can do the job” or “If this project doesn’t go smoothly, the whole team will suffer.”

Empathy can get in the way, too. When you see an employee struggling, it’s only natural to want to step in and help. But from the other side, this can feel more like micromanagement than support. And when leaders over-function by keeping too many tasks, they allow their teams to under-function.

Here are some strategies you can use to make delegation easier.

Shift from doer to leader mindset

In my corporate job, we promoted the best doers into leaders. This came with an assumption that they would magically shift from being good at and motivated by performance excellence and rewards to excelling at and caring deeply about developing others’ potential. The mindset shift may be the hardest part of all. So, how can you facilitate this in yourself?

Notice your payoff from doing. The thrill of achievement provides a quick dopamine hit. But that’s something you need to resist to get to the greater fulfillment of having helped others improve.

Claim your leadership identity by getting clear on values. Ask yourself: What three words do I want people to use to describe my leadership style? For example: Do I want to lead with control, urgency, and expertise? Or, with patience, curiosity, and empowerment?

Be intentional about responding, not reacting. In the moments where you are triggered to step in, ask yourself:  Would that be aligned with my values and who I want to become as a leader?

Embrace the discomfort of the learning process

Many leaders have said that, after witnessing an employee falter, taking back the work felt like the most supportive thing to do. But there is power to holding space for struggle. Yes, this creates discomfort for both leader and employee because it’s a new way of working for everyone. However, as Gallup reminds us, one of the keys to engagement at work is the opportunity for stimulating challenges. And when you push through the struggle, the result is growth for all parties.

How can you embrace, rather than resist, the struggle of learning?

Name your emotions, which according to psychologist Susan David, offers clarity and resiliency and can empower you to respond in an intentional way, aligned with your values.

Normalise being uncomfortable, embrace the struggle. Neuroscientists know that these are the periods in which learning happens and perseverance is developed.

Reframe the situation. One potential reframe is: “I was allowed to struggle and that’s where I gained confidence in my skills. So I’m going to give my employee the same gift of time to solve the problem on their own.”

Distinguish between high- and low-stakes tasks

Leaders often tell me they remain stuck as doers because employees make too many high-impact mistakes that require intervention. But this usually happens when the bosses themselves hold on to all the work for far too long and are then forced to delegate at the wrong moment. The key is to instead hand off tasks when the stakes are low and missteps tolerated, or even expected.

What makes an environment low-stakes? Failure will support learning more than it would hurt reputation. Mistakes will not impact team or company success. The environment is safe for stops and do-overs. The people involved have support and compassion for less experienced colleagues on learning curves.

To know which tasks are ripe for delegation, consider ones that now feel easy or rote to you but would be good development opportunities for those on your team? Also think about work that drains your energy and doesn’t align with your skills, talents, and strengths but might excite and feel like a perfect fit for others. 

For example, if your employee’s goal is to develop better presentation skills, try a low-stakes activity like asking them to lead the next staff meeting before a high-stakes one like conducting a client meeting. Or, if they want to get better at influencing others, challenge them to get buy-in from a small team on using a new tool or work process before asking them to persuade your whole division to implement it.   

Be curious and facilitative

Early in your corporate career as a trainer, people may tell me that you are visibly nervous during sessions you are leading. You may explain to your boss that I was worried about not having answers to participants’ questions. Her response: “What if your role isn’t to have all the answers but to facilitate the expertise in the room?” This changed my perspective.

Like trainers, leaders can’t be expected to have all the answers. But they do need to have patience and curiosity and ask insightful questions to facilitate learning. For example: What has your current approach been? Can you apply past experience to this problem? What is this situation teaching you?

Finally, practice compassion and grace. This doesn’t mean tolerating poor effort or careless mistakes. Instead, it means offering understanding and accommodation in the face of someone not doing something exactly how you would do it.

You got to have the courage to delegate to colleagues and team members even if it means watching them struggle. That’s the only way that all of us — leaders and employees — grow.


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During the demo, you will have the opportunity to explore the comprehensive features and functionalities of our psychometric assessments, experiencing firsthand how they can empower your HR strategies and drive positive outcomes. From personality assessments to cognitive abilities and team dynamics evaluations, our assessments provide valuable insights to enhance talent management and foster inclusive remote work environments.

Don’t miss out on this opportunity to test the power of unbiased HR solutions. Request your free demo assessment from Great People Inside today and embark on a journey of fair and effective talent management in the remote work era.

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Delegating Is Crucial & It’s Time to Stop Feeling Sorry About It

Delegating and its payoff is understood by most leaders: You free yourself to focus on higher-priority work while offering your team opportunities for growth and development. Whilst this is an excellent idea in theory, many good leaders struggle to put it into practice.

There are many reasons leaders don’t delegate. Some believe they’re the only ones who can do the job properly, or that it will take longer to explain than simply doing it themselves. Others don’t want to give up their role of go-to expert or fear being upstaged by their team. More recently, however, guilt about adding more work to a team member’s to-do list has been the primary obstacle voiced by the leaders I coach.

Take Kendra, a CMO at an advertising technology company, who stated, “I am so overwhelmed, but so is my team. I feel guilty asking them to do any more work.” Or Miguel, founder of a successful fashion brand, whose concern for his team led him to continually take on work he should have delegated.

Caring about the welfare of your team and managing their workload is part of good leadership. But when unchecked guilt gets in the way of delegating, it’s a no-win situation. Increased leader workload results in anxiety, burnout, and higher-value work going undone. Further, it can have damaging effects on the very team you are trying to protect. Employees can feel they aren’t trusted, which decreases morale and engagement, and a lack of growth opportunities leads to employee turnover.

Here’s how to alleviate your guilt and delegate more while still caring for your team.

Challenge your guilt

There are two types of guilt: justified and unjustified. When we have transgressed a moral norm, the uncomfortable but justified feeling of guilt activates our sense of responsibility and encourages us to make amends. Guilt also provides preemptive feedback, enabling us to be proactive in preventing misdeeds and boosting prosocial behaviour.

But when we wrongly assume responsibility for a situation or overestimate the suffering we might cause, guilt becomes irrational and unhealthy. Persistent unjustified guilt is associated with decreased self-esteem, increased anxiety, depression, and physical symptoms.

To distinguish whether the guilt you’re feeling is justified or unjustified, ask yourself, “What is stopping me from delegating this task?” and write down whatever thoughts come to mind. For example, Miguel wanted his team to like coming to work, so he took on more tasks (“I could be the one doing this”) rather than delegating them.

Challenge your thoughts. Ask yourself: How might I be wrong? What else could be true? Miguel realised that while it was true that he could do the work, it was not the right solution for the team or the company. If you’re not hurting someone or contradicting your morals, your guilt is likely unjustified.

Fact-checking your thoughts is especially important if you are guilt-prone, when any sign or possibility of another’s suffering and discontent can spur you to take undue responsibility.

Naturally, there will be times when delegating doesn’t make sense. However, you hold yourself and your team back when guilt results in a blanket approach of holding onto responsibilities that should be distributed.

Flip your script on delegating

People who feel guilty about delegating worry they’re burdening their team. They can also feel responsible for the happiness of others or believe the needs of others supersede their own.

Instead, recognise the benefits of delegating and reframe your thoughts. For example, consider that rather than burdening your team, you are giving them the chance to grow. Instead of believing that not delegating will promote team happiness, understand that people love feeling trusted by their leader. Allowing greater contributions and more meaningful work boosts engagement, commitment, and job satisfaction.

Hoarding work at the top is also a no-win situation for your company. Doing it all means you neglect work only you can do, and opportunities are lost. Delegation shifts work to the most appropriate level and pushes out the work that matters least. With the rapid pace of change today, leaders must frequently evaluate and eliminate work that is no longer relevant.

Improve your delegation skills

If you know you don’t delegate effectively, and this contributes to your guilt and reluctance, take action. The purpose of “healthy guilt” is to trigger positive change and make amends.

This requires intention and a reallocation of your time. Instead of doing, you lead and support. Start by assessing what’s on your plate and determining what you can delegate or delete altogether. Then consider who should take it on: Who has the need or desire to develop these skills or is ready for a new challenge?

It’s also helpful to involve your team in this process. For example, Kendra began regularly reviewing all areas of responsibility with her direct reports, asking “Where am I too involved?” and “Where do you need me to get more involved?” to ensure that her team members felt both empowered and supported.

Effective delegating extends far beyond the initial clarifying of desired outcomes and handoff. Set regular checkpoints for feedback, provide coaching along the way, and acknowledge team members for their contributions and achievements. Your improved delegation skills can help team members feel empowered, supported, and motivated.

Protect your team in different ways

When guilt prevents you from delegating, it often connects to an empathetic but misplaced desire to protect your team. Fortunately, there are other ways for you to safeguard your team, without the costs that accompany a lack of delegation.

For instance, help your team members ruthlessly prioritise their work. Proactively engage them in discussions about what work is currently on their plate and quickly eliminate low-value work from their list. Help team members work through competing priorities by clarifying and anchoring in the most important goals for your organisation and that person’s role and evaluating each task in terms of its importance and urgency.

Additionally, be mindful of shielding your team from external demands. Especially when more senior outside stakeholders make requests of your team members, it can be hard for them to say no. Be willing to step in where necessary to communicate a judicious “no” or “not now” to the stakeholder making the request.

Channel your protective instincts into safeguarding your team from low-value work. In supporting them and ensuring the work they do is meaningful, you can boost team member growth and satisfaction and assuage your guilt.

Prepare for temporary discomfort

Overriding guilt around delegation is not easy. Especially when you and your team are already time-strapped, it can feel misguided to invest in delegating. But remember this investment will unlock longer-term benefits: time savings and more capable, engaged employees.

No doubt there will be discomfort and setbacks as you and your team adjust to your new leadership style. Accept that mistakes will be made. When you’re prone to guilt, you may be quick to beat yourself up and question your decision to delegate. Instead, practice self-compassion, see these missteps as learning opportunities, and move on.

Delegating is a crucial aspect of good leadership; it demonstrates your trust in your team and gives them the opportunity to stretch and grow further in their roles. With some effort, you can learn to move beyond delegation guilt — and free yourself to lead more effectively.

Delegating is an artful dance between the manager and the employee, an intricate choreography that holds immense importance for both parties involved. It is a strategic practice that not only lightens the load for managers but also cultivates a fertile ground for growth and empowerment among employees. In this symbiotic relationship, the benefits ripple far beyond mere task distribution.

For managers, effective delegation is the key that unlocks the door to higher-priority work and strategic focus. It grants them the invaluable luxury of time—the most precious resource in today’s bustling business landscape. By entrusting capable team members with responsibilities, managers free themselves from the shackles of day-to-day minutiae, enabling them to elevate their gaze and delve into the realms of visionary thinking and impactful decision-making. Delegating becomes the gateway to unlocking their true leadership potential.

However, the significance of delegation transcends the realm of managerial convenience. It stretches its arms towards the employees, offering them a ladder to ascend in their professional journey. When entrusted with meaningful tasks and granted the autonomy to make decisions, employees are invigorated by a sense of ownership and purpose. The act of delegating communicates trust—a powerful catalyst for unleashing their full potential and driving motivation. It becomes a potent stimulant for growth, as they sharpen existing skills and acquire new ones, expanding their horizons and broadening their expertise.

Delegation also fosters a culture of learning and development within organizations. By affording employees the opportunity to tackle new challenges and stretch their capabilities, it ignites a spark of curiosity and hunger for continuous improvement. As they step out of their comfort zones, employees embark on a transformative journey, honing their skills, acquiring knowledge, and cultivating a deeper understanding of their own potential. With each delegated task, they become more versatile, adaptable, and resilient, fortifying the very foundation of their professional prowess.

Moreover, delegation cultivates a sense of shared purpose and collaboration. As managers entrust employees with meaningful responsibilities, they forge a connection rooted in mutual dependence and collective success. The manager becomes not just a boss but a mentor, guiding their team towards achievement while nurturing an environment of support and camaraderie. Team members, in turn, feel valued and acknowledged, fostering a sense of belonging and loyalty that transcends the boundaries of a mere employment relationship.

However, the art of delegation is not without its challenges. Managers must tread carefully, balancing the scales between empowering employees and providing necessary guidance and support. Effective delegation requires clear communication, well-defined expectations, and a genuine understanding of each team member’s capabilities and aspirations. It necessitates a willingness to step back and let others shine, knowing that their success is intertwined with the manager’s own accomplishments.

In conclusion, delegation is a represents a basket full of trust, growth, and collaboration, shared between managers and employees. It is an essential ingredient for managerial success and a catalyst for individual and organizational development. By embracing delegation as an art form and mastering its intricacies, managers can unlock untapped potential, while employees are granted the wings to soar to new heights. Together, they co-create a harmonious work environment, where each note resonates with purpose, engagement, and unparalleled achievement.


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Take the first step towards transforming your remote work culture by requesting a free demo assessment from Great People Inside.

Our team of experts will guide you through the assessment process, showcasing the effectiveness and value of our tailored solutions for your organization.

During the demo, you will have the opportunity to explore the comprehensive features and functionalities of our psychometric assessments, experiencing firsthand how they can empower your HR strategies and drive positive outcomes. From personality assessments to cognitive abilities and team dynamics evaluations, our assessments provide valuable insights to enhance talent management and foster inclusive remote work environments.

Don’t miss out on this opportunity to test the power of unbiased HR solutions. Request your free demo assessment from Great People Inside today and embark on a journey of fair and effective talent management in the remote work era.

Together, we can unlock the true potential of your remote teams and achieve remarkable success.Request a Free Demo Assessment.

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Delegation Is An Art: How Should It Be Done?

Delegation is a good idea but often falls flat in practice. Despite hiring bright minds and able hands, managers often find themselves overburdened and overloaded with tasks. Best practices tell individuals to focus on the highest priorities and delegate tasks to others, especially if it offers the opportunity for growth and development of your team. While this idea is great in theory, many people run into trouble.

A one-size-fits-all approach to delegation represents a strategy doomed to defeat. You could identify an item to delegate and then rely on the direct reports to figure out how to execute it or to speak up with questions if needed to. Unfortunately, not every item or even every employee is suited to this process, and problems can reveal themselves hours or minutes before a deadline. Here are four common reasons why delegation fails and what to do about them.

Lack of Critical Thinking

While many of us want to be considered smart, focusing on how others see you can be problematic when overplayed. If you jump in too early and too often with insights, your peers and direct reports will never have an opportunity to develop their own expertise. Confidence also takes a beating when people enter a meeting knowing they will leave feeling less than their manager. And while your insights may be helpful, they’re often offered only after a team has invested weeks of work preparing a presentation. It’s also dangerous to have only one person doing most of the critical thinking in an organisation; you could be leaving your company vulnerable to blind spots.

To elevate your team’s capacity to think for themselves, embed the practice of coaching early in the process. Instead of providing answers, ask questions. The quality of their insights will be directly proportional to the quality of your questions. For instance, by asking, “How would our chief competitor respond to this strategy?” Open-ended questions allow others to broaden their lens and consider new angles, rather than merely data-gathering queries. Instead of having to supply the solution, you activate others’ critical thinking skills.

Lack of Initiative

Sometimes employees lack the initiative to make bold moves or even follow up on smaller ones. They could agree to action items that they left incomplete or fail to communicate why they would miss a deadline. If you find yourself almost always initiating follow-up discussions then that is not delegating, that resembles micromanaging a lot more.

If your attempts at delegation are failing because you think others lack initiative or follow-through, address it tactically and strategically. Assign someone to jot down notes, action items, dates, and ownership before the end of each meeting, and start the next meeting following up on promises made. While this might sound basic, nearly half of the executive teams I work with lack appropriate hygiene in follow-through. More strategically, consider crafting a “placemat”— a one-page document (about the size of a placemat) that lists top priorities. A placemat signals what you plan to reward and provides another way to increase employee motivation. By scrubbing sloppy execution and signalling what truly matters, you can shape up accountability and motivation.

Lack of Quality

Unleash your team’s ability to contribute quality. First, provide them with a list of common mistakes in a presentation and what you would like instead. For example, instead of wordsmithing the title of a slide so it’s shorter, direct your team to deliver slide titles that don’t overflow to a second line. You can even delegate drafting this list to your direct reports based on what they already know about your preferences. Second, instead of fixing the fault, point it out and request a repair. Annotate a document with comments, instead of redlining it with direct edits. This will take more time initially but save you time in the long run as your team learns what you’re looking for. This may also require earlier deadlines, so your direct reports aren’t submitting final products at the last minute — and that’s ok. By showing them where they can improve, you’ll find that you’ll have better quality presentations and more time in the future.

Lack of Speed

Almost every CEO I have worked with marches to the beat of “CEO time” — a time warp where they either think they can (or they do) complete tasks faster than others. This may be the case because the CEO is more experienced, is clear about what she wants up front, doesn’t have to spend time divining or iterating to tailor the task, and hasn’t taken into account the extra time spent by employees because they want to look professional in front of the boss.

The next time you have what you consider a “quick” task, ask your team member how long they think it will take. If there is a discrepancy, ask about their process and the reason for the estimate. If necessary, you can help shave off time but removing unnecessary frills or details. For example, they may not need to create a beautiful slide deck but simply write up two paragraphs. On the other hand, you will start to become better educated about what and how long it takes to complete a delegated task and adjust your expectations accordingly.

Managers often experience the push and pull of delegation. We push out the work, only to pull it back again when it fails to meet expectations. By diving deeper into the point of failure, we can better address the underlying causes of delegation failure and encourage our team to be more motivated and productive.

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