22 Things Leaders Need to Say to Co-Founders and Employees When Things Just Ain’t Working Out

Written by Koko Ombu
Let’s face it. As entrepreneurs, sometimes things just don’t work out according to plan. The product launch got bungled; the best two developers just got nabbed by the competition; a prospective investor backed out at the last minute leaving others with cold feet, skeptical to move ahead as planned; funds are running out and it’s almost payday; the best client doesn’t want the deal anymore; a promising prospect turned down the promo offer; and the team is again failing to meet user and revenue projections for another month.
Nary can a startup founder or co-founders have a sweetened heart when faced with any of the above scenarios. Statistics from National Business Capital shows that 21.5% and 50% of startups don’t survive past the first and fifth years respectively. Despite when startups had high hopes and the most positive industry reviews and market analysis, there have been big fails (looking at you, Essential Products). So many leaders have been in this position, and no one knows this feeling more than Slack Founder, Stewart Butterfield.


One can only imagine everything that would have gone through his mind when Game Neverending, the online fantasy adventure company he started in 2002 with four co-founders, didn’t seem to be making any headway. He discussed with his team, and code was reinitiated out of the wreck to create Flickr, the popular photo sharing app.
Three years after being acquired by Yahoo for $25 million, he went on to create Glitch, another social fantasy gaming company which, despite receiving $17 million from investors, came crashing down. Stewart wept openly before his staff. Again, as a founding team coming together to discuss their next move; from the ashes of Glitch came Slack, worth $2.8 billion in just under 2 years and acquired by SalesForce for $27.7 billion in 2020.
As CEO and leader of the entire team, you are probably the convener of the top pack, and everyone looks up to you. You must understand that failures or setbacks are part and parcel of the business process. You should understand that despite the media’s depiction of founders as superheroes, you are human and vulnerable. Hence, what you say and do is reflective of your leadership capabilities and values. In times of challenges, what you say or don’t say can either make or mar the founding team and employees.
Companies can either burn out completely or still meet with great success at crucial times like Stewart Butterfield has been able to do.
Here are 22 things a leader can say to her co-founders and employees when things are just not working out:
- “I am here for the long haul.”
Is everything looking bleak from when you first ventured out with your co-founders? They need to know your stand with the company. ‘I am here for the long haul’ shows your commitment to what you started.
- “We are a team.”
As a leader, reinforcing team spirit is crucial to the stability of the founding team. It inspires increased collaboration and renewal for success.
- “We can do this.”
The toughest times are moments for motivation. Motivation will feed the inner spirit to surmount the present obstacles and cause the team to forge ahead despite the odds.
- “I am responsible.”
As a founder, if you realise your decision was directly responsible for a setback within the organization, your co-founders and employees are waiting for you to take responsibility for the error by saying it, even if they do not say this to your face. So, own up by stating it.
- “I am sorry.”
In tension filled moments, negative things could have been said, uncomplimentary remarks made, unbridled tempers flared, etc. This could be a time for sincere apologies. It could also be a time to apologise for putting undue pressure on teammates. You can never know how far these three soothing words “I am sorry” can go.
- “I understand how you feel.”
Some co-founders will be more emotional than others, so treat each person differently. Some will cry openly while some will hardly show emotions. As a leader, stay on each person’s level and show a great level of empathy towards everyone.
- “You all did a great job.”
Reminding the founding team of the awesome work they have been doing to bring the team this far is probably the most essential thing to do in both good and bad times. You never know when a seeming under performer could turn on the light bulb that will take the company to the next level. So keep the generous praises coming.
- “Smile – don’t take life too seriously.”
Ever heard the saying, “Don’t take life too seriously – you aren’t going to get out of it alive”? This is the time where humour could replace tears for people of gigantic emotional strength. Knowing things are not good but deciding to stay cheerful can introduce a form of relief for everyone.
- “Keep praying.”
Some people believe in a higher power. If members of the founding team do, tell them to pray for the company. It may be for renewed energy for everyone, new insights, new ideas, clarity and reestablishment of vision etc. Whichever way, it should be said and done together where necessary.
- “Take the weekend off.”
Leaders can work so hard they forget to even take weekends off. Perhaps it’s time to do the seemingly impossible – “take the weekend off, everyone.”
- “Let’s have lunch together.”
An exclusive lunch for the founders could be usual but making it something unusual with employees will help everyone relax, communicate freely, share perspectives and viewpoints on the company’s progress.
- “Let’s go for a retreat.”
Retreating after marathon work schedules is super important for any founding team. This should be translated into an energizer even when the team has been unsuccessful, as it is great for renewal of energy and focus.
- “Let’s go back to the drawing board.”
For any business owner, the drawing board is a muse, an experiential learning space and a restorer of hope in what is still possible and the need for re-evaluation and recreation in a time of crisis. Every leader should learn to “go back to the drawing board” and take the co-founding team along.
- “Let’s reassess our strategy.”
For any company not meeting expectations, a reassessment of strategy shows determination from the founder to uncover flaws within the team’s core strategy or product, operational or marketing strategy.
- “This is where we went wrong.”
You are all in the meeting already, and you have realised the point at which the company erred. Let everyone on the founding team be clear and in agreement on this point. “This is where we went wrong” should be certified by a nod from everyone and restated by you as a leader.
- “What do we need to learn from this?”
Asking the founding team the lessons they have learned from a bad situation can strengthen everyone. Don’t just take your lessons, but ask for theirs and learn from them. Like life in general, business offers continuous learning experiences.
- “Are our goals realistic?”
Company goals can turn bogus, especially when chasing numbers which can be influenced by investor goals or plain ego. This is a time for the team to collectively discuss if these goals can indeed be reached. “Are our goals realistic?” This may be hard for the previous goal setters to swallow, which most likely includes the founding team. However, addressing those goals when things are not going as planned can spell life or death for any startup or business.
- “We can innovate.”
A time of crisis can bring about myriad innovations. Co-founders and employees need to hear you remind them about this and your belief in them to stay innovative, which can buoy the company when in tumultuous waters.
- “Should we restructure?”
Ranging from the need for a new board member, a new mentor, understanding what others are doing and adapting to these leads etc., these could come from a simple question for restructuring. Restructuring even as a startup? Yes, even as a startup. It may be the business model, company values, operations etc.
- “We see your point of view.”
All ideas are worth being considered, and teams split when some members feel left out of the decision-making process or made to feel their ideas are being marginalized. As a leader, openly ask for feedback for each idea and remind each person of the importance of their viewpoint on the issue.
- “Hugs, everyone.”
Contrary to what anyone might think, a hug, a shoulder pat, holding of hands (all with consent!) even among adults can be reaffirming. After emotionally charged meetings, leaders can lighten up the atmosphere by asking for some good ol’ hugs. It never hurts, only heals.
- “Go spend time with family.”
Reassurance from family members who believe in an entrepreneur’s pursuits is critical. Almost every entrepreneur knows this. As a leader, you want to show your co-founders and employees that you remember they have people they love who can tell them how special they are. While startup founders are typically known to work ‘round the clock especially in the early stages, breaking up routine for some quality family bonding where applicable can be nothing short of reassuring.
Words have power. Words can heal. These 22 things your co-founders and employees need to hear you say when things ain’t working out are just a start. With some sensitivity and empathy towards those working with you on your startup or business, you can have the perfect words to say to keep the team thriving against all odds. So tell me, what else can you say to your co-founders and employees when things ain’t working out?
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