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Leading Through Change: A CEO’s Guide to Getting It Right the First Time

  • Kindred Works
  • Aug 22, 2025
  • 3 min read
Wooden cubes spell "CHANGE" on a light wooden surface. Soft focus background. Emphasizes transformation and new beginnings.

Change is hard. As humans, we are innately inclined to resist it because we crave certainty. 


But as a startup, the only constant is change. So how do you implement change quickly, confidently, and with minimal blowback? Unfortunately, the answer isn’t simple, but here at Kindred Works we have a recipe that works. Driving change starts with understanding how people, processes, and products will be impacted. From there, success is sustained through ongoing, consistent communication. Successful change takes time and effort, which may be why change efforts often fail to achieve their goals.


Let’s go through the common pitfalls and how you might remedy them to ensure your change sticks.


  1. Not understanding your “why”

    Every project, process, or product needs a clearly defined “why.” If there’s no clear reason for the change, you are guaranteed to meet resistance. And your definition of “why” may need to change depending on your audience. If you’re reorganizing teams, leadership might understand the landscape and market changes to which you are responding; however, individuals may feel lost as to why their manager or their role expectations are changing. Often your ICs are operating with less understanding than your leadership team, and it’s important to keep that in mind.


  2. Unclear project planning

    Once you understand and communicate the background of the change, you need clearly defined goals and a plan to address all the potential obstacles and risks in implementing this change. Your project plan should include deliverables, timelines, and clear ownership. There may be many moving parts, and each team should know how and when they will be impacted and how their job descriptions may change.


  3. Lack of buy-in

    According to McKinsey, 70% of change programs fail to reach their goals largely due to employee resistance and lack of management support. That adds up to a lot of wasted time and money. You might also have quiet resistance, i.e. people who agree publicly but complain to their peers. It may be helpful to have a “disagree and commit” rule, especially with your management team. You should present the project to your leadership team to allow for questions and feedback. But once you’ve addressed concerns, encourage your team to support the change publicly, even if they still have some doubts.


  4. Failure to onboard and train teams

    You’ve laid out a project plan and followed through on the major action items, but does everyone know what is expected of them going forward? Have you detailed all the places in which the process may change? This is an important step in ensuring the change actually sticks and performance can be managed properly going forward. You’ll want to have clear documentation and training sessions for your current employees, along with changes to onboarding materials for new employees.


  5. No plan for reinforcement

    Even if you have buy-in, people have habits that they may need help changing. It will be important to communicate often to remind the company what’s expected going forward. It is said that you need to repeat something 5-7 times in order for it to stick (more if the information is complex). While that may sound excessive, you can share the information in multiple channels - email, meetings, training sessions, your company wiki, and Slack. This also accounts for people who learn things in different ways: some need a visual, some need to hear it out loud, etc. You can also detail how managers should handle reinforcement, encouraging them to mention it in team meetings and give feedback in 1:1’s.


  6. Unclear or non-existent feedback mechanisms

    As with any new project or goal, there will be questions or concerns that need to be addressed. There should be feedback loops embedded into the plan. If you’ve defined your “why” and presented it to leadership, make sure you take time to hear and address their concerns before moving forward with addressing the company as a whole. It is also helpful to offer escalation points for ICs to raise questions and concerns, which means managers will need to have all the information required to respond appropriately.


Any of these pitfalls can derail your progress, but with good planning, clear outcomes, and timely followthrough, you can implement change that accomplishes your goals with less pain.


If you need help with implementing change, Kindred Works can do it with clarity, enthusiasm, and intention. You can contact us here to hear more. 

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