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How Great Leaders Overcome Common Challenges to Achieve Success

By 03/04/2023June 20th, 2024No Comments

Business leadership can be a tough job. A lot can land on your shoulders, and diaries fill up fast. You can find yourself torn between handling your own work and helping your team grow and improve while you’re stuck in seemingly endless meetings.

Nearly all leaders face the same issues: workload overwhelm, diary management and the challenges of working with bosses and peers. Here we’ll be giving you advice for overcoming these commonalities so you can move forward and succeed as a leader.

Workload Overwhelm

We hear this from leaders time and time again; they’re too snowed under to feel like they’re getting anything done. What most are really saying is that they’re struggling to develop their team and delegate to them.

This is a case of not seeing the woods for the trees. Without effective coaching, empowerment and delegation, your team can’t support you.

1. Effective Delegation

Delegation doesn’t mean palming off the work you don’t want to do. It needs to be carefully considered and strategic- both in terms of your workload and in terms of helping your team to develop their skills.

The four Ds approach can be a great starting point. Start by listing your current tasks under these headings:

  • Do: Work that only you can and should do (make a prioritised list and get it done)
  • Delay: Work that you need to do, but that can wait (diarise and set reminders)
  • Delegate: Work that needs to be done but could be handled by a member of your team
  • Drop: Work that you/your team don’t need to be doing at all (go back to the requester and explain why this doesn’t fall within your remit)

Now, take your delegation list and separate these tasks out, identifying which are:

  • Tasks that will potentially develop an individual, giving them skills, behaviours, or knowledge they need to progress.
  • Tasks that align with an individual’s current skill set and natural strengths.
  • Tasks that will provide variety without challenging or developing an individual.

You now need to take a good, hard look at your team. Identify your over-performers (those working above expectations) and your steady eddies (reliable members of the team who consistently work to expectations).

MadeYou founder, Luke Todd explains the importance of concentrating on delegating tasks that feed into your team’s current skill sets and motivations:

While over-performers are a natural go-to for delegation, you need to ensure that they are consistently over-performing in all areas before delegating. Don’t underestimate your steady eddies either- they may appreciate some variety, with new tasks that don’t necessarily stretch them.”

Luke ToddMadeYou Co-Founder


  • If a task is a low risk but more complex in nature, it should be listed under number 1 and given to an over-performer.
  • A high-risk task should be listed under number 2 and given to the ideal overperformer.
  • If a task is both low risk and simple, it should be listed under number 3 and can go to a Steady Eddie.

If you and your team are new to the world of delegation, you may encounter some teething problems- these are worth pushing through. Some common issues include team members not following your guidance, tasks taking longer than expected, and you feeling a lack of control. These are all avoidable by making sure you’re setting clear expectations for each task, providing as much guidance and support as needed and sticking to the skillset of your team. Patience is key, and results will follow.

2. Empowering Your Team

Based on your team’s skill set and potential, you should always be looking for ways to develop and empower them- for the sake of their success and yours.

The first step in making your team feel empowered is to stop micromanaging them. Take a hard look at your current practises- could they be construed as micromanagement, even if that’s not your intention? You hire great people to do great work- support and guide them but let them but let them do their thing.

Aim to put the right processes and reporting in place to support micro visibility (having an overview of what’s going on), then you won’t need micromanagement. Make sure you’re also consistently available for support without blame or criticism.

Luke ToddMadeYou Co-Founder

Great empowerment can be supported by encouraging your team to work together, sharing ideas, asking each other for help and offering support. Involve your team in your decision-making and watch them strive to achieve what they’ve been a part of planning.

You can also let them lead their own 1-2-1 sessions by asking what’s gone well for them and what’s not gone so well for them since you last spoke. This allows the employee to guide the conversation, flagging where they may need more support and highlighting areas where they’re succeeding.

Investing in external business coaching is the next step in empowering your employees. It allows them to focus on their individual development with someone not related to the business, which can only make them a stronger player for the team.

3. Coaching Your Team

Taking a coaching approach to steady eddies and overperformers can be incredibly effective. A coaching leader is supportive but also challenging; not afraid to set challenging goals but also offers regular feedback and guidance.

Leaders that utilise this style will set clear goals and expectations while upholding a positive and motivating environment. Employees know what’s expected of them, they’re continually encouraged to grow and learn (which bolsters their skill sets), and their weaknesses are often turned into strengths.

This approach can be a great tool to use when your staff are asking questions they’re not yet feeling empowered to answer for themselves. You can help them find the answer rather than answering it for them and effectively stalling their progress.

Meeting Mania

Most leaders can relate to this; a diary so full of meetings that there’s little space left for your own work and for spending the time you need to on your team and their progression.

This issue boils down to two solutions: effective time management and enforcing meeting etiquette.

Handling Meeting Requests

First on the tick list is to require an agenda, or at least an objective, for any meeting requests you receive. If it’s a meeting about a meeting, run for the hills. If a pinpointed agenda or objective isn’t available, we suggest you at least ask yourself the following before accepting:

  • How are you feeling today?
  • What are you hoping to get from this meeting?

This gives you a chance to decide if you’d be in the room for the right reasons and if you’d be able to give the meeting the focus it needs. If it’s a yes, go ahead and accept. If it’s a no, you should then ask yourself:

  • Is there anyone else in the business who would be better placed to attend based on the agenda/objective/my check-in?

If all else fails and you’re still drowning in meeting requests, you can:

  • Suggest a company-wide “no meetings day” to give everyone a chance to catch up, uninterrupted.
  • Time-block your calendar for the tasks you need to get done regularly and refuse any meeting requests during those times.
  • Simply start saying a polite “no” by suggesting a different time/date or asking if the meeting could take a different format such as a communal document, a video or a call.

Sending Meeting Requests

If you’re the one suggesting a meeting, timings really matter. Avoid starting/ending meetings on the hour or half-hour. Too often, meetings are booked like this, and it doesn’t allow attendees any time to prep for the meeting, nip to the toilet or grab something to eat between their other commitments.

Everyone, including you, needs a little time before and a little time after to make notes and to let the outcome of the meeting percolate. Never go straight from one meeting to another- the information will not be processed properly.

Equally, prescribing an hour for a meeting means that the hour will be filled regardless of necessity. Try sending the invite for 10:06 – 10:50 instead of 10:00 – 11:00. You may find that people arrive more prepared, are more focused and get more out of the meeting overall.

Top Tip: You can ensure that this approach is used by others through some careful manipulation of your own calendar. Block out your time until 11:03. Anyone looking to book a meeting will see you’re unavailable and book it in for 11:30, giving you the space you need.

Limiting the number of attendees is also wise. Ideally, there should be no more than 8 people in the room unless it’s a project-steering meeting. Avoid inviting anyone for whom the content is an ‘FYI’ and simply follow up with them afterwards.

You’ll get far better results by holding shorter meetings for those who truly need to be there than by trying to discuss multiple topics in one longer meeting where half the room will switch off during the topic that doesn’t affect them.

Human Relations

No man (or woman, obviously…) is an island. While new leaders will likely focus on managing their team to deliver results, progression will rely more and more on working well with colleagues from outside that direct sphere. This means that great relationship-building and the ability to work through or around conflict are key skills for leaders.

Effective C-Level teams work together as a cohesive unit to benefit the business. They’ve learnt by that point in their careers that collaboration is key, regardless of personality type and human nature.

Think about the boiler you need fixing at home. You may get frustrated with the plumber, but you manage yourself. If you break down the relationship you won’t get your boiler fixed- especially if he’s the only plumber available…It’s no different in the workplace.

Luke ToddMadeYou Co-Founder

It’s impossible to like everyone you work with, so working through conflict and prioritising collaboration is crucial. You need to set aside your need to be right and work together for the good of the business.

Knowing yourself and what your dominant leadership style is can be so helpful. Different people need different approaches- one size does not fit all.

Adapting your leadership style to suit the people you need to work with (and the situations you need to work with them in) can avoid the majority of workplace conflict. Give them what they need from you rather than what you think they should get.

You need to make sure you’re utilising your dominant style only for those that it suits while actively working on the other styles to build a toolbelt for members of the team who require a different approach.

Great leaders understand their limitations. They know they may not be the best person in the room for a particular task and know how to utilise their resources, including those around them. Always use your resources rather than restricting them due to ego. You’ll come across better to others, and you’ll go further.

Our top tips for working well with your peers:

  • Make decisions among yourselves instead of delegating the decision to a higher-up.
  • Communicate in an open and timely way to avoid nasty surprises.
  • Ask for and provide help wherever needed.
  • Avoid poaching (or even appearing to poach) your peer’s team members- open communication is key.
  • Give feedback directly, never via a higher-up.
  • Approach your peers as teammates rather than competitors.

MadeYou can support Leaders in so many ways, including via our Leadership and Business Management Skills courses. These are ideal for Senior/Heads of/Directors and Middle Managers respectively and equip attendees with the skills needed to succeed in the leadership of others.

Want to become the best version of yourself as a Manager? Fill in the form below, and we can let you know which of our resources may be best for you:

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