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Why Sidekick agencies SMASH the initiative

Updated: Sep 11, 2023

Sidekicks across the country use our “Take more initiative” feature to ask the players they are checking in about opportunities to lead the way as they face challenges big and small. Every few days players are asked questions that improve the odds they’ll solve these problems and come to their managers with solutions.



Training a team to take more initiative is a valuable investment in building a proactive and high-performing workforce. Encouraging initiative not only boosts productivity but also fosters a culture of innovation and continuous improvement. Here are steps to train your team to take more initiative:

  • Set Clear Expectations:

    • Start by clearly defining your expectations regarding initiative. Explain what it means to take initiative in your context and why it's important for the team and the organization.

  • Lead by Example:

    • As a leader, demonstrate the behavior you want to see in your team. Be proactive, take ownership of your responsibilities, and show a willingness to go above and beyond.


  • Communicate the Vision:

    • Share the organization's vision and goals with your team. Help them understand how their initiative and contributions align with the bigger picture.

  • Create a Supportive Environment:

    • Foster a culture where taking initiative is encouraged and rewarded. Ensure that employees feel safe to voice their ideas and concerns without fear of criticism.

  • Provide Autonomy:

    • Give team members the autonomy to make decisions within their areas of responsibility. Empower them to take ownership of tasks and projects.


  • Set SMART Goals:

    • Establish Specific, Measurable, Achievable, Relevant, and Time-bound (SMART) goals for individuals and the team. These goals provide clarity and motivation for taking initiative.

  • Acknowledge and Reward Initiative:

    • Recognize and reward team members who demonstrate initiative. Publicly acknowledge their efforts, whether through praise, bonuses, or other incentives.

  • Foster Collaboration:

    • Encourage collaboration and idea sharing among team members. When employees work together, they often generate innovative solutions and motivate each other to take initiative.


  • Provide Training and Resources:

    • Offer training and resources that equip your team with the skills and knowledge they need to take initiative effectively. This might include problem-solving workshops, creativity training, or leadership development programs.

  • Offer Constructive Feedback:

    • Provide regular feedback on your team's performance, highlighting instances where they've taken initiative and suggesting areas for improvement. Use positive reinforcement to reinforce the behavior you want to see.

  • Delegate Responsibility:

    • Delegate tasks and projects that challenge team members and encourage them to stretch their capabilities. Ensure they understand the importance of their contributions and the impact on the team's success.


  • Encourage Risk-Taking:

    • Create a safe space for calculated risk-taking. Encourage your team to propose new ideas and solutions, even if they carry some level of risk. Discuss the potential benefits and drawbacks openly.

  • Continuous Learning and Development:

    • Promote a culture of continuous learning. Encourage team members to seek out opportunities for skill development and personal growth.

  • Provide Mentoring and Coaching:

    • Pair less experienced team members with mentors or coaches who can guide them in taking initiative and making sound decisions.


  • Celebrate Successes and Learn from Failures:

    • Celebrate achievements and milestones resulting from team members' initiatives. Likewise, use setbacks or failures as learning opportunities to improve and adapt.

  • Monitor Progress:

    • Regularly assess and monitor your team's progress in taking initiative. Adjust your training and support strategies as needed to reinforce positive behaviors.


  • Regular Check-Ins:

    • The heart of the Sidekick check-in process is quick daily check-ins. It is invaluable to hold regular one-on-one or team meetings to discuss progress, challenges, and opportunities for taking more initiative. Use these discussions to provide guidance and support.

  • Create a Feedback Loop:

    • Encourage open and honest feedback from team members. Ask for their input on how to improve the team's culture of initiative and address any obstacles they face.

By implementing these strategies, you can create an environment that fosters a culture of initiative within your team. Over time, this culture will not only lead to increased individual and team performance but also contribute to innovation and the achievement of organizational goals.



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