Asking for Help: A Challenge or an Essential Step Working Remotely?

Asking for Help: A Challenge or an Essential Step Working Remotely?
Photo by nikko macaspac / Unsplash

There is no such thing as a complete expert, and asking for help can sometimes feel like a burden, while at other times, it feels like a must-do. When working remotely, asking for help has a new perspective. Before we jump into this edition of the newsletter, let's look at what people said about "asking for help" before and after COVID-19 and after everyone experienced working from home.

On-Site Work: A survey by the Bureau of Workplace Dynamics in 2020 revealed that 75% of employees in traditional office settings felt comfortable seeking help from their colleagues or superiors. The proximity and daily in-person interactions contributed to a culture where seeking assistance was viewed as a natural and encouraged behavior.

Remote Work: In 2021, a survey by RemoteWork Insights found that only 40% of remote workers reported feeling more comfortable seeking help than their on-site counterparts. The challenges of virtual communication and the absence of face-to-face interactions contributed to a reluctance among remote team members to seek assistance proactively.

These findings underline the impact of remote work on the willingness of employees to ask for help. Remote leaders should recognize and address these shifts in behavior to cultivate a supportive culture in virtual environments.

In this edition, we will cover the following topics:

  • What are the challenges leaders should consider when working remotely?
  • What is the importance of having a supportive help culture?
  • How can leaders build this help culture?
  • What strategies can be used to improve your team's help culture?
  • When and how should leaders seek help?

Let's dive in!

The "Asking for Help" Challenges for Remote Leaders

There are a lot of common challenges that leaders face while working remotely; here, we will focus on the ones that impact the team's help culture and support.

In fact, those are some of the top issues many companies ask their people to return to the office. Being aware of the challenge and its possible solutions can boost your team to a more high-performing level 🚀


  • Challenge: The physical separation of team members can lead to isolation and detachment.
  • Impact: Reduced camaraderie, potential misunderstandings, and a lack of team cohesion.
  • Addressing the Challenge: Regular virtual meetings, team-building activities, and fostering a sense of belonging through open communication can mitigate the effects of physical distance.

Personal Connection:

  • Challenge: The absence of in-person interactions can hinder relationship-building and team bonding.
  • Impact: with a less personal connection, it's harder to ask for help from each other. Some team members are introverts and need personal relationships to ask for help.
  • Addressing the Challenge: Organizing periodic in-person meetings (when possible), creating informal communication channels, and letting people work together (Pairing) can foster a sense of connection among remote team members.

Process Clarity:

  • Challenge: lack of clarity on the "HOW" the team should react to situations and everyday problems they face while working alone.
  • Impact: This leads to gaps in how to deal with issues, and without clear protocol and process, the team will lose time and often take the wrong approach to the solution as it's not a defined standard for the team.
  • Addressing the Challenge: Document your teamwork and how to do it. This way, there will always be a reference for them to find. Also, keep track of the team processes and ensure every process is clear for everyone (Like how to ask for help?)

Remote leaders who proactively address these challenges contribute to a more positive and productive remote work environment. Later, we will discuss those strategies in depth, but before, let's understand when and how leaders should seek help. 

By knowing this, leaders can become the example that the team can look up to and become better at asking for help.

When and How Leaders Should Proactively Seek Help:

Recognizing Complexity:

  • When: When faced with complex challenges or decisions beyond the leader's expertise.
  • How: Initiate discussions with subject matter experts, seek mentorship, or consult with team members possessing relevant knowledge.

In Times of Uncertainty:

  • When: During periods of uncertainty or ambiguity where multiple perspectives are beneficial.
  • How: Facilitate open discussions within the team, encourage diverse viewpoints, and actively seek input from team members.

Managing Overwhelm:

  • When: When overwhelmed with tasks or responsibilities.
  • How: Delegate tasks, communicate workload constraints, and seek support from team members or superiors in prioritizing and strategizing.

Handling Interpersonal Issues:

  • When: Dealing with complex interpersonal conflicts or team dynamics.
  • How: Engage in open and honest communication, consider seeking assistance from HR or external mediation services, and prioritize team-building initiatives.

Balancing Work and Well-being:

  • When: When struggling to maintain a healthy work-life balance.
  • How: Discuss workload concerns with superiors, explore flexible work arrangements, and prioritize self-care practices.

Learning from Mistakes:

  • When: After making a significant mistake or encountering a setback.
  • How: Reflect on the experience, seek feedback from relevant stakeholders, and implement strategies to avoid similar issues in the future.

Technological Challenges:

  • When: Facing technological challenges or changes.
  • How: Engage with IT experts, attend training sessions, and encourage team members to share their technological insights.

Building New Skills:

  • When: When aiming to acquire new skills or knowledge.
  • How: Enroll in relevant courses, attend workshops, and seek mentorship from individuals with expertise in the desired area.

Proactively seeking help demonstrates leadership strength, humility, and a commitment to continuous improvement. Leaders who recognize the value of collaboration and actively seek assistance contribute to a resilient and agile organizational culture.

Let's examine the team members' views and understand why they avoid asking for help.

Why People don't ask for help?

Many of us see asking for help as a point of weakness; however, that is not always the case, and in many cases, asking for help is an opportunity to learn something new. Here are 8 Psychological Factors Behind Hesitation to Seek Help:

  1. Fear of Judgment:
    • Individuals may worry about being perceived as incapable or inexperienced, leading to concerns about judgment from peers or superiors.
  2. Perceived Weakness:
    • There might be a societal or organizational stigma attached to asking for help, with some individuals associating it with weakness or a lack of competence.
  3. Concerns about Competence:
    • Individuals may fear that asking for help implies a lack of expertise or skill, potentially undermining their professional reputation.
  4. Self-Reliance Mindset:
    • A cultural or personal inclination towards self-reliance can create a mindset where individuals must solve problems independently to demonstrate autonomy.
  5. Imposter Syndrome:
    • Those experiencing imposter syndrome may hesitate to seek help, fearing that doing so will expose them as a fraud or someone who doesn't belong.
  6. Previous Negative Experiences:
    • Past experiences receiving unhelpful or judgmental responses when seeking assistance can create apprehension and reluctance to repeat the process.
  7. Perceived Burden on Others:
    • Individuals may worry about burdening colleagues or superiors with their problems, leading to hesitancy in seeking help.
  8. Cultural Norms:
    • Cultural norms emphasizing individualism or downplaying the importance of seeking assistance may influence behavior in specific contexts.

As a leader, you should be on the lookout for the above reasons for your team not to share that they need help, and to do so, here are 12 strategies you can consider as tools to help create a fantastic, supportive, and culture of help in your organization/team.

Strategies to build and improve the team help culture

Following these steps and strategies will help you and your team to be more empathic, supportive, and helpful to each other, which will lead into 

✅ Better collaboration and communication.

✅ Better outcomes and results.

✅ More empowered team members.

✅ Less work stress and mental burnout.

1. Cultivate a Positive and Inclusive Environment:

  • Encourage Open Communication: Emphasize that open communication is valued and welcomed.
  • Promote Inclusivity: Ensure every team member feels included and their opinions are respected.

2. Lead by Example:

  • Demonstrate Vulnerability: Share instances where you sought help or clarification.
  • Encourage Questions: Explicitly communicate that asking questions shows curiosity and growth.

3. Establish Clear Communication Channels:

  • Define Communication Guidelines: Clearly outline how and when team members should communicate.
  • Use Collaboration Tools: Leverage tools that facilitate easy and open communication, such as messaging apps and video conferencing.

4. Provide Regular Feedback:

  • Constructive Feedback: Foster an environment where feedback is seen as a productive tool for improvement.
  • Positive Reinforcement: Acknowledge and provide positive reinforcement for team members who actively seek clarification.

5. Conduct Regular Check-Ins:

  • Scheduled Meetings: Hold regular one-on-one and team meetings to check in on progress and address concerns.
  • Open Door Policy: Emphasize your availability for impromptu discussions and questions.

6. Foster a Learning Culture:

  • Promote Continuous Learning: Encourage ongoing skill development and learning.
  • Share Resources: Provide access to educational resources and materials that facilitate learning.

7. Establish a No-Blame Policy:

  • No-Penalty Environment: Assure team members that asking questions or seeking help will not lead to negative consequences.
  • Focus on Solutions: Shift the focus from blame to finding solutions collaboratively.

8. Organize Team-Building Activities:

  • Virtual Team-Building: Arrange activities that promote team bonding and create a sense of unity.
  • Icebreaker Sessions: Start meetings with casual conversations to build rapport among team members.

9. Celebrate Mistakes as Learning Opportunities:

  • De-stigmatize Mistakes: Communicate that making mistakes is a natural learning process.
  • Learning Reviews: Conduct post-mortems or learning reviews after projects to extract lessons and encourage open discussions.

10. Provide Mentorship Opportunities:

  • Assign Mentors: Pair less experienced team members with mentors who can offer guidance.
  • Promote Mentorship Programs: Encourage team members to seek mentorship actively.

Conclusion: We must build a supportive culture as we adapt to remote work. This is not a one-time goal but a continuous journey that requires commitment and effort from everyone involved. We should create an environment where team members feel comfortable asking for help and where such requests are accepted and celebrated. By doing so, we can empower our teams to achieve higher levels of productivity, collaboration, and success.

Thank you for joining us in this learning journey to build teams that help and support each other.