How To Navigate Challenging Work Requests

How To Navigate Challenging Work Requests

What is your best tip for responding to challenging work requests made by a coworker, your boss, or an internal department?  

To help you navigate challenging work requests, we asked CEOs and business leaders this question for their best advice. From asking for help from coworkers to understanding the motivation behind the request, there are several guiding tips to help you navigate and respond to challenging work requests. 

Here are 10 strategies for navigating challenging work requests:

  • Ask for Help From Coworkers
  • Communicate and Ask for Help
  • Approach it as an Opportunity To Learn
  • Break Down Task Into Manageable Steps
  • Ask Questions for Clarification
  • Document All Communication During The Project
  • Respond Positively But Avoid Guarantees
  • Seek Clear Guidance
  • Be Assertive But Open To Compromise
  • Understand The Motivation Behind The Request

How To Navigate Challenging Work Requests

Ask for Help From Coworkers

It’s always difficult to deal with challenging requests at work, but I see it as an opportunity to grow and build deeper connections with your coworkers. When you have a challenging work assignment to deal with, try asking your coworker for help. There’s always somebody in the team that can help, perhaps some of the senior members with lots of experience. If they are unable to help you directly, they can always suggest some good ways to deal with the situation and help relieve some pressure off your mind. This is also an opportunity to build deeper connections with your coworkers and grow together through challenges.

Harry Campbell, The Rideshare Guy


Communicate and Ask for Help

When you have a challenging accommodation request from someone at work, figure out your game plan and communicate. Take a step back and re-analyze the request and see if it is unreasonable or just challenging. If it is something that makes sense but is going to be a challenge, start breaking down the problem into small attainable steps.  Communicate with the person with the request and provide updates and don’t be afraid to ask for help.

Sumeer Kaur, Lashkaraa


Approach it as an Opportunity To Learn

See the challenging work as an opportunity to learn more about a process, system, or method to make it easier for yourself and the department in the future. Perspective is everything. Even something as “challenging” as organizing tax documents or expense reports is an opportunity to find new organizational systems to make them easier to find in the future. Maybe your own home can benefit from this new system of filing that you learn? Or if you’re tasked with learning the Amazon selling platform with no experience think of the marketable skill that you will have for the future. Remember, the challenge won’t last forever, but the perspective you can gain from it can.

Jason Reposa, Good Feels


Break Down Task Into Manageable Steps

Work with the requestor to break down what they want into manageable steps. Agree on benchmarks where they review your work to ensure you’re on track. This will make the assignment a collaboration rather than resting all on your back, even if you’re doing most of the work. By the time you finish the assignment, it’s already been tacitly approved by your teammate.

Patricio Paucar, Navi


Ask Questions for Clarification

Ask questions. It’s way better to clarify the details of a challenging work request rather than stress over the logistics of it. In order to carry out any task, you have to first understand what is expected of you. It’s ok to ask for clarification if needed. Communicate any comments, concerns, and especially questions to ensure that you are properly equipped with everything you need to meet a challenging request. Make sure you put your best foot forward by asking clear questions to your coworker, boss, or an internal department to fully understand the request.

Ray Leon, Pet Insurance Review


Document All Communication During The Project

The more challenging the request, the higher the likelihood there will be miscommunication. Follow up every phone call and discussion during the project’s duration with an email summary of the conversation. The first email should be a detailed reiteration of the project scope and goals including completion date. Remember, summarize every conversation, no matter how trivial or short and before long you’ll earn a reputation for being buttoned-down, one of the highest forms of praise in the business world.

Nirav Sheth, Anatta Design


Respond Positively But Avoid Guarantees

Challenging work requests should be met with a response that is openly optimistic yet does not guarantee a particular outcome for the request. Bosses, coworkers, and the heads of internal departments will appreciate communication that shows a positive effort. However, employees need to give themselves some room to fall back on if the work request is challenging to fulfill. Employees should not try to guarantee an outcome if it will come at a significant cost to themselves. It’s important to keep in mind that a can-do attitude will benefit an employee’s reputation in the workplace. With that being said, challenging work requests should not be fulfilled at the individual expense of an employee.

Katy Carrigan, Goody


Seek Clear Guidance

Being asked to take up an unfamiliar task by a boss or other work authority can be nerve-racking. All too often, the expectation that you should ‘know’ how to do any assigned tasks can lead to feelings of embarrassment when you need to ask for a follow-up. Don’t let those feelings hold you back, the most important thing is to be able to complete a request efficiently and competently.  In the long run, asking for guidance when you need it will save time for all involved parties. Try asking for an example of the work that’s required of you, vetted by the person assigning the task. Use that example as a guideline, even if you feel like you’re just copying someone’s overall design. Depending on the task, uniformity may be preferred over adding your own style to an assignment. Nothing trumps communication when it comes to doing a job right. Reach out when you need to so you can get things done right the first time.

Caleb Ulffers, Haven Athletic


Be Assertive But Open To Compromise

It’s not easy to be assertive, especially in the work environment. On the one hand, you want to be helpful and support your organization, but on the other, you might have other responsibilities that stop you from doing extra things. Firstly, keep in mind that there is nothing wrong with saying “no” as long as you don’t hurt others. You shouldn’t agree to something just because you want to be nice to others. Why? Because then you hurt yourself! That’s why it’s essential to find a balance between your needs and those of others.  

My advice is to hear the request, ask about its details, and think if you’re the right person to complete it. If so, ask your requester to give you some time to decide. Then, consider what level of commitment you can offer and if you have all the needed tools and resources to get fully engaged. In your response, be assertive and don’t make promises you can’t deliver. Be willing to compromise, but remember about your own commitments you want to be faithful to.

Dorota Lysienia, MyPerfectResume


Understand The Motivation Behind The Request

To deal with a challenging work request, you need to understand the person’s motivation. In most cases, the request is for a justifiable purpose. So, instead of arguing about it, try to work with the person and figure out why he or she is taking this so personally. Offer your help to find a solution that works for everyone. If you can understand why the person is making this request, you’ll have a much easier time convincing him or her that your solution is the best one.

Tomoko Harris, WinnerWinner


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