How to Prevent Failure in Working From Home to Address the COVID-19 Coronavirus Pandemic

10 min read

So many organizations are shifting their employees to working from home to address the COVID-19 coronavirus pandemic. Yet they’re not considering the potential disasters that can occur as a result of this transition.


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An example of this is what one of my coaching clients experienced a few months before the pandemic hit. Pete is a mid-level manager in the software engineering unit of an entrepreneurial startup that quickly grew to 400 office-based employees doing Electronic Health Records (EHRs). He was one of the leaders tasked by his company’s senior management team with shifting their employees to a work-from-home setup, due to rising rents on their office building.


Specifically, Pete led the team that managed the transition for all 400 employees to telework, due to his previous experience in helping small teams of 3 to 6 people in the company transition to working from home in the past. However, the significantly larger number of people they had to assist now was proving to be a challenge. 


So was the short amount of time available to this project, only four weeks, before the company had to pay a lot of money for a month-by-month temporary lease extension on their office building. Ideally, this transition should have taken several months, but talks with the building owners about a financially viable long-term lease extension broke down, putting the company in a tough spot.


Pete reached out to me while he and his team were being inundated with countless emails with general inquiries and requests for priority, among others. With so many stakeholders and a tight deadline, he needed help sifting through all the things he needed to attend to and wanted to make sure he executed decisions efficiently. Paramount on his mind as well was to ensure that the security of patient information is not compromised during and after the transition.


Pete was right to be careful. After all, mid-size and small businesses have their share of catastrophes in implementing decisions and managing projects and processes. Such mistakes largely come from the many dangerous judgment errors that result from how our brains are wired, what scholars in cognitive neuroscience and behavioral economics call cognitive biases.


Fortunately, recent research in these fields shows how you can use pragmatic strategies to assess and defeat these mental blindspots to avoid decision-making disasters in your business, in your relationships, and in other life areas. But what do you do after you make a critical decision, such as to shift your employees to a telecommute setup? You also need to avoid failures and maximize success in implementing these significant decisions, as well as in managing projects and processes that result from these decisions. 


The most relevant scholarship in implementing decisions deals with prospective hindsight, meaning looking back in advance. Prospective hindsight helps you anticipate and avoid threats as well as notice and seize opportunities. Thus, you can defend yourself against failures and maximize the likelihood of success in major projects and processes, and in implementing decisions.


8 Key Steps to Preventing Disasters in Working From Home


I recommended that Pete apply the “Failure-Proofing” strategy, which is a pragmatic and easy-to-use technique for obtaining the benefits of prospective hindsight. Having developed this technique based on behavioral economics and cognitive neuroscience studies, I then tested it on the front lines of my over 20 years of experience consulting and coaching leaders in large and mid-size companies and nonprofits to avoid project or process failures.


Use Failure-Proofing after you make any substantial choices to ensure success in implementing decisions. Likewise, use it to assess major projects or processes you are about to launch or which you are currently managing. The failure-proofing technique is best done in teams, and should involve representatives of all relevant stakeholders; you can also do this technique by yourself, but consider showing your results to a trusted adviser for an external perspective.


Step 1: Gather all relevant stakeholders


Gather all the people relevant for making the decision in the room, or representatives of the stakeholders if there are too many to have in a group.  A good number is 6, and avoid more than 10 people to ensure a manageable discussion.


Make sure the people in the room have the most expertise in the decision to be made, rather than simply gathering higher-up personnel. The goal is to address what might go wrong and how to fix it, as well as what might go right and how to ensure it. Expertise here is as important as an authority. At the same time, have some people with the power to decide how to address problems and seize opportunities that might be uncovered.


It’s very helpful to recruit an independent facilitator who is not part of the team to help guide the exercise. You can get someone from your Advisory Board, someone from another part of the organization, your mentor, or a coach or consultant. If you are going through this technique by yourself, write out various stakeholders that are relevant to the project or process, even different aspects of yourself that have competing goals.


Pete decided to gather 6 stakeholders composed of one manager each from the 4 departments that urgently needed to be shifted to a work-from-home setup, as well as one team leader each from the two teams which would provide auxiliary support to Pete’s team while they were facilitating the transition of the teams. He recruited Anne, a member of the firm’s Advisory Board, to be an independent facilitator.


Step 2: Explain the Failure-Proofing process to prevent failure in implementing decisions, or in project and process management


Explain the Failure-Proofing process to everyone by describing all the steps, so that all participants are on the same page about the exercise.


Step 3: Develop two Next Best Alternatives (NBAs) to the current plan for implementing the decision, or managing the project or process


Then, develop two Next Best Alternatives (NBAs) to the plan for the decision, project, or process you are evaluating. Have each participant on the team come up with and write down one NBA anonymously. Anonymity is critical to ensure that unpopular or politically problematic opinions can be voiced (“perhaps we should wait for a better opportunity rather than acquiring this company”).


The facilitator gathers what people wrote – thus ensuring anonymity if the facilitator is not part of the team and doesn’t know people’s handwriting – and voices the alternatives. Then, have team members vote on the choices that seem most viable, and choose two to discuss. Make sure to give them a fair hearing by having two team members – including at least one with authority – defend each NBA.


After discussing the NBA, take an anonymous vote on whether the NBA seems preferable to the original project or process under discussion. If the original project or process still seems best (which is what happens in the large majority of cases), consider if the project or process can be strengthened by integrating any components of the two NBAs into your plan. If you are going through the technique by yourself, get outside input at this stage if you have difficulty generating an NBA.


Ann, the independent facilitator for Pete’s discussion group, reviewed the current plan with the participants. The plan was to shift all 400 employees to a remote work setup in four weeks. Everything – even business meetings – would be done online after four weeks. 


Most of the participants in Pete’s discussion group voiced out that the tight deadline was a problem. Staff needed to prepare their homes for a telecommute setup: some needed a better Internet connection, while others did not have a quiet space to work from their homes – yet. These details needed to be ironed out at the staff level. 


Another problem raised by some members of the discussion group was that despite being an EHR firm, some documents and processes weren’t 100% digital yet. This could not be solved hastily as the security of patient information should not be compromised in any way. 


An additional issue that came up was that there were critical on-site meetings with external firm stakeholders that were scheduled months in advance. The managers and staff involved needed to convert these to online meetings first. 


After identifying these issues, Ann asked the participants to come up with one NBA each, write it down on a piece of paper, and submit it to her once they were done. She asked the participants not to write their names down, to keep the process anonymous. After she had all the pieces of paper with her, Ann read out all the NBAs suggested, after which the participants voted on the top two NBAs. 


After voting, Ann read out the two NBAs which garnered the most votes. The participants then proceeded to discuss these NBAs, with one staff member and one manager defending each NBA:


  • The first NBA was to make the move in batches of 100 employees per week. One of Pete’s team leaders from the software engineering unit and an HR manager reasoned that by using this NBA, they would be able to identify and respond to “birth pains” from the first batches and refine the process to benefit the succeeding batches.
  • The second NBA was to stick to the four-week plan but only have three-fourths of the firm working from home after four weeks. One-fourth of the firm’s employees would remain in the office as a skeletal team composed of key people from each department during an additional two-week transition period. Pete and a team member from the Finance unit reasoned that by using this NBA, there would be employees in the office who could take care of unfinished tasks, such as finalizing digital files or attending meetings that cannot be shifted online yet. The problem with this plan would be paying for a lease extension, which would be very costly.

After further discussion, the discussion group decided to merge the current plan with the first NBA, taking into consideration the issues raised for the current plan and the solutions presented in the second NBA.


The final plan: Pete’s team would migrate the 400 employees to a remote work setup in four weeks, but will be doing so in batches of 100 employees per week, using the following guidelines: 


  • The first batch would be composed of employees of varying ranks from all units, so that Pete’s team can clearly identify birth pains and refine the process to benefit succeeding batches. As much as possible, the first batch will also be composed of employees who did not have any on-site meetings scheduled with any external firm stakeholders. Also, C-level executives will work on-site until the fourth week as well, to give more time to complete meetings or shift them online. 
  • Only 10% of the records division would be joining this first batch. The remaining 90% will work on site and will only be migrated on the fourth week. This would give the division time to ensure that all documents and processes have been shifted to a digital form. 
  • The second and third batches will also be composed of employees of varying ranks from all units. Pete’s team would be able to tweak the migration process after observing the birth pains from the first batch.
  • Finally, everyone left onsite by the fourth week should be migrated to telecommuting by the close of the week. It is also the fourth batch’s responsibility to ensure that all assets – physical or digital – have been moved or stored properly. 

After agreeing on these guidelines, Pete’s discussion group was able to proceed to the next step. 


Step 4: Imagine that the decision, project, or process definitely failed, and brainstorm reasons for why your plan failed


Next, ask all the stakeholders to imagine that they are in a future where the project or process definitely failed (an approach informed by the Premortem technique). Doing so gives permission to everyone, even the biggest supporters of the project or process, to use their creativity in coming up with possible reasons for failure.


Otherwise, their emotions – which determine 80-90% of our thoughts, behaviors, and decisions – will likely inhibit their ability to accept the possibility of project or process failure. That’s why simply asking everyone to imagine potential problems works much less well. Supporters of the project experience a defensive emotional response that leaves their minds much less capable of creatively envisioning possible problems.


After giving such permission, have each participant anonymously write out plausible reasons for this disaster. Anonymity is especially important here, due to the potential for political danger in describing potential problems (“the product launch will fail because the marketing department overhyped it, leading to unhappy consumers). Ask everyone to come up with at least three most plausible failures, while highlighting that the reasons for coming up with these failures is to address them effectively.


These failures should include internal decisions under the control of the project team, such as cost and staffing, as well as potential external events, such as an innovation introduced by a competitor. Encourage participants to focus particularly on reasons they would not typically bring up because it would be seen as rude or impolitic, such as criticizing someone’s competency, or even dangerous to one’s career, such as criticizing the organization’s strategy. Emphasize that everyone’s statements will remain anonymous.


The facilitator gathers everyone’s statements, and then highlights the key themes brought out as reasons for project failure, focusing especially on reasons that would not be typically brought up, and ensuring anonymity in the process. If you are going through this technique by yourself, write out separate reasons for project or process failure from the perspective of each relevant aspect of yourself.


Going back to Pete’s group, everyone submitted their anonymous reasons for failure. Ann read out the participants’ anonymous statements, highlighting the following key themes:

  • The plan failed because it wasn’t communicated in a clear and timely manner. One of the participants raised doubts that management can communicate the plan efficiently due to past cases of miscommunication of company policy changes.
  • The plan failed because without a physical presence, the Human Resources and Finance divisions were not able to address issues in an empathetic and precise manner. A participant stated that some HR and Finance cases raised by staff were sensitive in nature and required face-to-face interaction with HR and Finance personnel. Without this, the statement read, employees might feel disconnected from the company and eventually leave. 
  • The plan failed because the project team didn’t explain technical terms simply enough. A participant raised the issue that some staff and managers from the software and technical teams – including Pete – were not always proficient in explaining technical terms so that non-technical employees can understand them. This could lead to employees having a difficult time in comprehending technical specifications and requirements. 

Step 5: Decide on the most likely and serious problems leading to failure


Discuss all the reasons brought up, paying particular attention to ones that are rude, impolitic, and dangerous to careers. Check for potential cognitive biases that might be influencing the assessments. The most significant ones to watch out for are loss aversion, status quo bias, confirmation bias, attentional bias, overconfidence, optimism bias, pessimism bias, and halo and horns effect.


Then, assess anonymously the probability of each reason for failure, ideally placing percentage probabilities. If doing so is difficult, use terms like “highly likely”, “somewhat likely”, “unlikely”, and “very unlikely.” Also consider how harmful each reason for failure might be, and pay more attention to the ones that are most harmful.  Here, the expertise of individual members of the team will be especially useful.


The leader or person assigned as note-taker writes down all the problems brought up, as well as assessments of the probabilities. If you are going through the technique by yourself, get outside input at this stage.


In Pete’s case, the participants agreed that all the key problems brought up in Step 4 – lack of communication, lack of physical human connection, and confusing technical instructions – were somewhat likely, based on historical issues the different divisions had experienced in the past. 


Step 6: Brainstorm ways to fix problems and integrate your ideas into the plan


Decide on several failures that are most relevant to focus on, and brainstorm ways of solving these, including how to address potential mental blindspots. Also, discuss any evidence you might use that would serve as a red flag that the failure you are discussing is occurring or about to occur. For this step, it is especially important to have people with authority in the room.


The leader or note-taker writes down the possible solutions. If you are going through the technique by yourself, get outside input at this stage.


Circling back to Pete, the managers who were part of the discussion group took on the task of addressing the problems proactively:


  • Pete will discuss the issues tackled in the discussion group with senior management. He will then propose for senior management to send out immediately a company-wide announcement on the migration to telecommuting and the steps that will be taken. Then, each senior manager would have in-person meetings with their direct reports in middle management, to get their buy-in and ensure that the message passed effectively down the chain of command. In turn, the middle managers would meet with the frontline staff and work out details of the next steps for each team.
  • The HR manager will coordinate with other division managers to ensure that empathetic practices will be observed before, during, and after the transition to remote work. After senior management sends out its company-wide announcement, HR will then send out communications of its own, to emphasize that employees will remain connected through digital platforms and apps and that issues and concerns will still be addressed quickly. They’d also offer to meet personally with employees to address any and all concerns. 
  • Finally, Pete will meet with his migration team to ensure that technical requirements and specifications will be communicated using the simplest of terms and that processes are not made too complicated for the end user. After coming up with a final technical plan, he will send out his own email to all employees – to introduce his team and outline the steps that they will be taking in the next four weeks. Then, he would have an in-person meeting to discuss next steps with his team. Likewise, Pete would run his communication plan by HR to ensure his understanding of “simple terms” aligned with HR’s perception of how frontline staff would respond to the messaging. 

Step 7: Imagine that the decision, project, or process succeeded spectacularly, brainstorm ways of achieving this outcome, and integrate your ideas into the plan


We addressed failure: now let’s make sure you not simply avoid failure, but maximize success! Next, imagine that you are in a future where the project or process succeeded far beyond what you expected. Have each participant anonymously write out plausible reasons for this success. Next, have the facilitator highlight the key themes.


Discuss all the reasons, and check for the same cognitive biases as above. Evaluate anonymously the probability of each reason for success, and decide which deserve the most attention. Then, brainstorm ways of maximizing each of these reasons for success.


The leader or note-taker writes down the ideas to maximize success. If you are going through the technique by yourself, get outside input at this stage.


In Pete’s discussion group, Ann asked each participant to anonymously write out the reasons for the plan’s success. When Ann read out the statements, there was one key theme: They imagined that the plan succeeded because everything was communicated clearly and in an efficient manner. It also helped that Pete’s migration team, the division managers, and senior management were responsive and quick to reply to inquiries. Because of this, doubts and concerns were easily assuaged and problems were easily identified.


Step 8: Revise the overall plan based on this strategic exercise


The leader revises the project or process based on the feedback, and, if needed, repeats the exercise.


Pete got in touch with me two weeks after his project was completed to tell me some good news: his teams successfully executed the plan and all 400 employees were, by then, working efficiently from the comforts of their own homes. While there were some bumps along the road during the first week, his team’s responsiveness and the support from the other division managers helped pave the way to a smoother transition from the second through fourth weeks. 




To prevent work-from-home disasters in this time of transitioning to manage the COVID-19 coronavirus pandemic, make sure to use the “Failure-Proofing” technique prior to implementing decisions of any significance, as well as to assess the management of substantial projects and processes. To see case studies with in-depth guidelines of how you can apply this strategy as an individual or a team, see the Manual on Failure-Proofing.


Key Takeaway


To prevent disasters in transitioning to working from home, imagine that your transition completely failed. Then, brainstorm all plausible reasons for failure, and generate solutions to these potential problems. Do the same to maximize success. Click to Tweet


Questions to Consider (please share your thoughts in the comments section)


  • What questions do you have about applying this technique when shifting your organization to a telecommute setup? 

  • Where do you think Failure-Proofing might best fit into your organization’s work-from-home process? 

  • What will be your next steps in most effectively bringing it to your team and integrating it into your organization’s remote work processes? 

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Bio: Dr. Gleb Tsipursky is on a mission to protect leaders from dangerous judgment errors known as cognitive biases by developing the most effective decision-making strategies. A best-selling author, he wrote Never Go With Your Gut: How Pioneering Leaders Make the Best Decisions and Avoid Business Disasters (Career Press, 2019), The Truth Seeker’s Handbook: A Science-Based Guide (Intentional Insights, 2017), and The Blindspots Between Us: How to Overcome Unconscious Cognitive Bias and Build Better Relationships (New Harbinger, 2020). He has over 550 articles and 450 interviews in Fast Company, CBS News, Time, Business Insider, Government Executive, The Chronicle of Philanthropy, Inc. Magazine, and elsewhere. His expertise comes from over 20 years of consulting, coaching, and speaking and training as the CEO of Disaster Avoidance Experts, and over 15 years in academia as a behavioral economist and cognitive neuroscientist. Contact him at Gleb[at]DisasterAvoidanceExperts[dot]com, Twitter @gleb_tsipursky, Instagram @dr_gleb_tsipursky, LinkedIn, and register for his free Wise Decision Maker Course.