10 Creative Leadership Challenges and Solutions in 2023 and Beyond

2022 has been a transformative year for creative teams and the ones that lead them. The recent changes have brought on high rewards, together with a new set of challenges. Let us dive deep into the top creative leadership challenges and solutions that will keep everybody talking in 2023 and beyond.

10 Creative Leadership Challenges and Their Solutions

1. Keeping Up with Accelerated Growth

The Challenge: Content is king – and it reigns supreme. The demand for and supply of entertainment is more widespread than ever before, and creative teams are feeling the heat – 38% of in-house brand and creative teams reported output growth to be reaching a fever pitch. Aside from adding new members to meet demand, one of the biggest challenges of creative leaders is keeping their team happy when increasingly more is asked of them every day. Constant growth may be what the corporate doctor ordered, but creative employees are frequently at odds with that.

The Solution: Perform regular pulse checks. Praise your team members for their demanding work. Ask them how they are doing, and if, and where, they may need assistance. Urge them to gauge their week at work through weekly check-ins. Be open to their feedback and keep communication transparent and constant. If you notice someone working long hours, provide them with the support they need as soon as you can.

Need to streamline your creative operations?

Ready to power your brand?

Let us show you how the Lytho platform helps in-house creative and brand teams do better work and keep stakeholders on brand.

2. Inspiring Creative Team Members

The Challenge: This is such an obvious one – and yet, it is one of the most-cited creative leadership challenges. We can see it clear as day, the logical fallacy that is – creativity requires inspiration and, therefore, every creative individual must be a well of self-producing inspiration for themselves and those around them… right? Creative people can experience a lack of inspiration just as much – and as often – as everyone else. Finding pleasant, meaningful ways to inspire your team can go a long way.

The Solution: Creative people like creative approaches – knowing your team members’ hobbies and interests is key here. Take the time to discover and involve them in activities that you know they will be potentially interested in. And what is the link between such activities and inspiration, you may ask? The process itself, of course! It has been scientifically proven that when we engage in meaningful activities, the brain regions responsible for creativity, inspiration, and everything artsy light up – that is when the ideas start flowing.

3. Managing Stakeholder Expectations

The Challenge: AKA the bane of leaders’ existence across fields, industries, time zones, countries, and continents. This is the toughest one of the three, as it is the one that is tied to externals the closest. You and your team may be experiencing one of your best weeks or quarters in terms of generating innovative ideas, exploring novel concepts, and giving shape to what may become your next signature thing and most forward-thinking industry first that will certainly cement your position on the pioneer table.

And yet, despite all this, If the numbers do not add up, you have done all of this for nothing. At least according to data-driven stakeholders. Balancing such a relationship can be so tricky as there are so many ways things can go wrong, since there are so many bases to cover. What sits at the heart of this age-old struggle is the different definitions of and measurements for success.

The Solution: Creative people measure success by the quality of their output, data-driven people do so by looking at numbers. Let us be real, you cannot hope for a utopian, meet-each-other-halfway kind of scenario here. But what you can do is maintain a frequent feedback loop between sides. In this way, expectations will be better adjusted over time, and clashes will be kept to a minimum. You can read more on the specifics for this one at Forbes by clicking here.

4. Finding and Retaining the Right People

The Challenge: We are currently seeing an unprecedented surplus of opportunities, combined with record shortages in the workforce. And it is not happening to a handful of countries only – the issue is global. It is obvious that it is tough to find the right personnel and make sure they stick around long term. Add record inflation numbers to the mix, and you get to our present job market climate, where job seekers have a plethora of opportunities to choose from, and employers are becoming increasingly desperate to fill essential positions.

This is a perfect storm of a job market, where the tables have turned, and employees hold more power than before. So how do you attract, and keep attracting, the right people? How can you stand out in a sea of corporate sameness? And how do you ensure you select the right fit, and not whoever is willing to take up the job?

The Solution: Qualitative research on the issues of employee attraction and retention abounds. Look at the infographic on the right for the benefits of employee retention. The most influential study conducted on the topic suggests two main themes that will significantly boost your chances of success:

4.1 Provide Great Compensation and Benefits

This is straightforward – the most competitive employer in this area wins the right people over and gets to keep them the longest. We recommend you follow these steps in revisiting the salary range, benefits package, and other incentives you offer:

  • Establish as high a budget as you are comfortable with

Employees will only feel that you truly value them and wish for them to remain with the company long term if you show your appreciation with tangible rewards. If business objectives need to be measurable and all, should not employee objectives be the same? Be generous with your potential future employees and the job market will return that generosity.

  • Increase flexibility in how and when work gets done

Long gone are the days when people would have to come into an office five days a week, from 9am till 5pm minimum. The pandemic, for all its challenges, taught us a valuable lesson – that of remote work and trust. Creative leadership in 2022 entails allowing people to get non-urgent work done when it is convenient for them. The way we now think about work has shifted dramatically – and employees wish for work to exist next to their personal lives, not against it.

4.2 Increase Employee Morale

The other factor impacting employee retention immensely is the atmosphere at work. It is useful to ask yourself the following questions in revisiting your workplace:

  • What is the company culture like and what could be improved?
  • Do you organize enough events so employees can create memories together?
  • Are you providing employees with adequate personal and professional development opportunities?
  • How do you deal with conflicts in the workplace?
  • Do employees feel they are heard and supported by the organization?

Need more on employee retention? Employee Retention: 10 Strategies for Retaining Top Talent

5. Inapt Requests

The Challenge: Creative leadership and teams have spoken, and we have listened! As outlined in our Q3 2022 Creative Operations Report, almost half of creative teams are faced with inapt requests. When receiving requests for creative work, many senders lack a solid understanding of the creative process. The result? Creatives receive work that they struggle wrapping their heads around. Meanwhile, their stakeholders think the team is taking too long and asking too many questions. The result? Unnecessary back and forth that:

  • Costs valuable time
  • Creates a lot of frustration for both sides
  • Causes the creative team delays in completing their projects

Our Review + Approval tool offers Online Proofing so you can:

5.1 Stop Endless Feedback Loops

Deliver clearer, more actionable feedback in real time, using the following features:

  • Intuitive drawing, text, and canvas tools for clear feedback.
  • @Mention feature that lets you direct feedback to the right people.
  • An instruction function that allows designers to create specific instructions before sending proof.

5.2 Remove Project Bottlenecks

Your feedback, located in one place. Save yourself the headache by:

  • Streamlining all feedback sent and received so you eliminate misunderstandings.
  • Verifying edits easier than ever before with side-by-side comparisons.
  • Gaining clearer insights into what each of your team members is working on.

5.3 Revisit Work w/ Streamlined Collaboration and Approvals

Can you imagine a world where your projects are not delayed by late approvals from stakeholders? Our software makes that a reality. With Online Proofing, you can:

  • Specify whose approval is needed and in which order.
  • Choose if a reviewer’s approval is essential or non-essential.
  • Accelerate the approval process with customizable templates based on department, type of asset, and any other criteria.

Read this to improve your request intake process: Tips to Perfect Your Creative Intake Process

6. Ad-hoc, Last Minute Changes

The Challenge: This is one of the most unpleasant issues, and it occurs often – too often. Imagine work on a project is almost complete. Everyone involved is feeling proud about what they have accomplished. A lot of planning, thought, mental and physical labor have gone into turning a suggestion to a fully realized product. You think the worst is behind you and have planned for some downtime to recharge your creative batteries.

Suddenly, a last-minute change turned everything around. You switch from relaxation mode to an anxious state way sooner than you would have liked to. Instead of taking it easy like you wanted, you are now stuck with figuring out how the change impacts every aspect of the project. Storytelling? Needs to be amended. Visuals? Need to be thrown out of the window, much like your patience has at this point.


The Solution: Be strategic in how you approach such changes. No one likes to revisit work and make changes to it, so keep that firmly in mind. Know the personalities in your team well enough to deliver the news in the best way possible. Try the following:

6.1 Understand What Influences the Changes

It helps to gain a firm grasp on where the change is coming from, and whether it is influenced by budgetary, data, or resource-driven changes. Knowing why such a last-minute change occurs helps justify the need for it for yourself and others.

Before responding to the request, take a few minutes for yourself to consider if this is a reasonable request. When you respond, do so in a way that communicates that this is not something that should reoccur, independent of whether you accept or decline the request.

Set firm boundaries in communicating that you and your team have your own workload to deal with already, and that such requests should be communicated way in advance.

6.2 Assess the Impact and Brace Yourself for It

Make sure you answer the following questions before moving to the next step:

  • Is the request a nice-to-have or necessary?
  • Which areas of the project will be impacted?
  • How big is the impact on each area?
  • Does your team have the capacity to make the requested changes happen?
  • Who needs to be involved in implementing the changes?

Have all the answers you need? Great, you can now move to the hardest part, if applicable.

6.3 Communicate the Changes to Your Team

This is the most crucial step in the process and the one likely to involve the most resistance from project participants. You need to make sure that you:

  • Convey your appreciation for your team’s extensive work on the project.
  • Communicate the changes and the reason for them clearly.
  • Are open to and accept all frustrations your team expresses.

Once all the above is said and done, read the following article on What Makes for an Effective Creative Brief to minimize or prevent this from happening in the future.

7. Too Much or Too Little Feedback

The Challenge: Let us face it – providing feedback is a minefield. Hence, the distinction between positive and constructive feedback. This topic can be so loaded that we have scared ourselves away from ever using the work negative in association with it. Lack of feedback is an equally complicated topic that gives rise to uncertainties and confusion. There are plenty of reasons why feedback is such a hotly debated and carefully approached topic:

7.1 Feedback is personal

We can spin this any way we wish and start the conversation with generalizations, claiming this is an organization-wide issue, and insisting that the feedback about to be provided is directed at the individual’s work. We stress how it is meant to contribute to their betterment, and reiterate it is not meant to be taken personally, since we are all fabulous unicorns with no personality flaws. And yet, if all of this were true, then why do we all feel so terribly anxious when receiving or giving it?

7.2 Feedback has a time and a place

A group of scientists conducted a very influential experimental study on providing solicited and unsolicited feedback, where they examined the effects that providing feedback has on both the provider and the receiver. The experiment asked participants to provide feedback in two different manners – a solicited and an unsolicited one.

The results? Participants felt uncomfortable and anxious when giving or receiving feedback in both scenarios. Their heart rates were racing, their palms were sweating, but researchers found a key difference. When a person provided feedback to another in a respectful and expected manner, everyone felt better. Receivers took the feedback better, and providers felt less guilty and could be more assertive in future interactions. In contrast, when participants provided feedback unexpectedly, both them and the targets of the feedback suffered more. And get this – the givers of unsolicited feedback felt so uneasy that they softened their communication in future interactions. This made them come off as less assertive and more agreeable.

7.3 Lack of feedback causes uncertainties

People have a universal affinity for well-defined things. We like to know what we have to do, where we stand with work and the people around us. Ambiguity is not our best friend, to put it mildly. So, it makes sense that too little feedback can have an undesired influence on our work. Are we doing the right thing? Should we be doing something differently? Are we doing enough? This constant questioning can be debilitating.

7.4 Lack of feedback creates wrong assumptions

On the other end of the spectrum, the most confident among us may take a lack of feedback as a sign that we are doing everything right. This can be a double-edged sword since overconfidence can blind us to improvements and may hinder our personal and professional progress and growth.

The Solution: The STAR Constructive Feedback model. Use the STAR model to receive and provide specific, fair, actionable, and solicited feedback. This model emphasizes five key components that should always be taken into consideration before and during the feedback process:

  1. People: How will people relate to the feedback?
  2. Strategy: What methods will you use in providing it?
  3. Structure: How do you formulate and direct the conversation?
  4. Processes: Which processes does your organization have in place?
  5. Rewards: How are you going to reward feedback actioned?

Credit: Petadiri

In Providing Feedback:

1. Find out all you can about a situation, like:

  • Who was involved?
  • What happened?
  • And when did it happen?

2. Define the task at hand by:

  • Looking at the primary objectives.
  • Homing in on the (part of) the assignment that went well or awry.
  • Contextualizing any setbacks or wins that occurred during execution.

3. Next, know what action was taken:

  • What actions did your colleague take in response to the task at hand?
  • Are the actions they took sufficient or insufficient?
  • For constructive feedback: Remember it is crucial that you avoid sounding critical at this stage.

4. Discuss the results:

  • What was the outcome of their actions or lack thereof?
  • Did their actions help complete or hinder the objective?
  • For constructive feedback: Suggest what they can do differently in the future.

In Receiving Feedback:

1. Ask for a meeting agenda beforehand:

Knowing what the topic of discussion is going to be will help you prepare for a pleasant or tough discussion ahead. Knowing this will help you stay composed and moderate your emotions better. While challenging discussions are never pleasant, knowing that you will be having one makes all the difference in the world.

2. Write down what went well and what you can get better at:

This tip will help remind you of your worth – writing down everything you have contributed to the team and the company can act as a buffer to feelings inferiority and imposter syndrome that may arise in tough discussions. Bring that list with you and go over it, if necessary, before responding to questions. Similarly, take note of what you could have done better so you can ground yourself better – trust us, this will make for a fruitful discussion.

3. Take the time to distance yourself from the situation:

Is the upcoming feedback session simply good news? Great! Then, feel free to skip this step. If you have any doubts though, take a few minutes to reflect on your behavior and performance in the last few weeks. Be honest with yourself about what you excelled at and admit your shortcomings. This will reduce conflicts and misunderstandings during your talk.

4. Listen first, speak later:

This advice is as old as wisdom itself and it can be quite challenging to implement. When you interrupt your interlocutor or respond too quickly, you run the risk of upsetting them, misunderstanding their point, and your feelings will most certainly get in the way of progress and growth. Good luck!

8. Keeping Up with Digital Trends

The Challenge: Digital technologies advance at an unprecedented pace, making it next to impossible for creative teams and leaders to keep up with trends. New tools emerge all the time, together with systems, software, and processes. What we regard as innovative, and current is already yesterday’s news when we read about it. And in the middle of it all, creative people are expected to stay informed and complete their work on time. Simply put, most creative professionals must choose between the two. We cannot dedicate enough time to both without severely compromising other areas of our lives.

The Solution: Not all hope is lost – approaching this creative leadership challenge with a plan is key. Try the following sequence:

8.1 Identify pertinent tools and be critical of potential ones

Just because there is a flashy new tool out on the market does not mean you need it to complete your work. As a leader, you need to be able to distinguish between must-haves and nice-to-haves. First, ask yourself if you have all the tools, you and your team need to carry out your tasks. Then, decide whether the new tool you are considering will be impactful enough to warrant the trouble of switching to it.

Read more on a solid framework for considering new tools here.

8.2 Add professional development as an objective

Do you need your team to stay abreast of the competition? Then, the most effective way to achieve that is by making time and room for professional development and training. Allocate budget and time at your preferred cadence (every week, month, or quarter) for your team to hone their skills. You can train people in new tools, the latest trends, and valuable people skills at the same time.

Read Glassdoor’s Professional Development Goals piece here.

8.3 Reevaluate workloads

If all else fails, you may want to revisit your employees’ workloads. You see, often, both employees and leadership have the best intentions when defining professional development, but often fall short when allocating time for it. Consider the following:

  • What work is crucial to core functions in the short term?
  • What work is crucial to core functions in the long term?
  • How long does each task need to be completed?
  • Are said tasks distributed evenly or unevenly among team members?
  • Do you have team members who have taken on too much work?
  • Do you have team members who have taken on too little work?
  • Which non-essential tasks can be performed by specialists only?
  • Which non-essential tasks can be performed by everyone in your team?

Once you have answered the above, you should have a clear picture of how work is distributed in your team. From there on, approach your team and explain the benefits of shuffling certain tasks around. You can now move on to the last step.

8.4 Find specific personal development and training materials

Congratulations! You have completed the hardest part of the process. Now, it is time to speak with your team members about what they want their professional development to look like. Offer advice and guidance and remind them that you are more than happy to allocate resources for their development if they can tie it back to pertinent business goals.

Read more on Reevaluating and Re-balancing Workloads here.

9. Having the Right Creative Operations Tools

The Challenge: Our technologically advanced landscape dictates that most basic task tools are not enough anymore. Creative teams are too often stuck in endless feedback and rework loops that push back deadlines, make creative work more stressful than it should be, and subtract and distract from business goals.

Complicated processes like the ones mentioned above demotivate creative teams and often lead creative professionals down the road to burnout. There is nothing worse than a team of exhausted creatives who cannot perform to the best of their abilities.

The Solution: A creative operations suite, like Lytho’s, is just what you need to break feedback loops, accelerate, and improve project planning, management, and execution, and store all your creative assets in one place, so you know where everything is, always.

Read more on how to prevent burnout and keep your creative team motivated here.

10. Giving Your Creative Team Authority


The Challenge: Creative teams are often treated like order-takers. What is worse, the highly creative professionals that make everything happen are the last ones to be notified of the impending work. Picture the following:

It is a Friday afternoon, and you are wrapping up your work week, getting ready for a relaxing easing into the weekend. Suddenly, you receive a last-minute email or meeting invite where you are informed of the urgency of work you were not even aware existed until now. Whether you push back or not, you are reminded that this is an urgent task that must be completed before the end of business today. Three thoughts may run through your mind:

1. You refuse to comply with the request and risk facing disgruntlement, pushback, and the reminder that if this is not completed then it will have a negative impact on the business and someone else will have to do the work in your stead.

2. You begrudgingly agree to get the work done and you keep telling yourself and the requester this is the last time you accept such a last-minute request. And, unfortunately, you know full-on well that it will not be the last.

3. On the one hand, you want to prioritize your well-being by logging off on time and leaving at 5:30pm sharp. On the other hand, you are fully aware of the negative impact doing so will have on your employer. A lose-lose situation.

The Solution:

If we suppose that creative teams are just as responsible as their stakeholders for being treated like order-takers, what are specific actions can your team take to change that? Here are some actionable steps that your creative team can start using today to begin moving towards a more strategic partnership:

  • Be fearless about asking why – after all, it is the requester that has come to you with a last-minute change, and it is them that will benefit from your work the most. Find the underlying cause of the request and remind them that they should follow standard procedure for future requests.
  • Begin the conversations on project support needed from the creative team before a project has even been kicked off. Instead of silently accepting a request without a fight, demand that the requester be present and available to answer all questions relating to the project and its goals. And demand that they do so as they lay out their project plan, not when the project is at its final stages before completion.
  • Embrace a video or in person call – rather than hiding behind emails and messaging applications, opt for the most direct approach when dealing with such requests. Speaking to people face-to-face allows you to be more thorough and assertive.

Concluding Remarks

Creative leadership challenges are as old as the first moment in history when business and creativity merged. The point of this series is to help inspire potential solutions to and aid you in dealing with your creative leadership challenges with a flexible mindset. It is okay to try different things and find what works best for you and your team. Remember, these challenges have been around for a long time and will continue to follow creative teams around for the near future. Think big and act with bravery. Thank you for joining us in this creative leadership challenges journey!

Are you interested in tools that will help you address current creative leadership challenges and provide you with the support needed for future ones? Lytho helps you streamline your entire workflow and harmonize all brand collateral under a single, uniform platform. Feel free to reach out to us by scheduling a demo and learning how our creative solutions can boost the effectiveness of your creative projects. We look forward to speaking with you!