Five Conversations CEOs Must Have With Their Teams Before End of Year

September has a way of changing the mood in a business.

The year is not over, but suddenly the end is no longer a distant event. There are only a few months left to achieve the targets set at the beginning of the year, recover lost ground, collect outstanding money, close important deals and deal with problems that have been postponed for too long.

For a CEO, this is the time to start asking difficult questions because there is still enough time to do something about what the answers reveal. A good CEO should not arrive in December and suddenly discover that sales have fallen far below target, expenses have quietly eaten into profits, key employees are frustrated, customers are leaving, or an important project is nowhere near completion.

The end of the year should not be a surprise to a good CEO. This is particularly important at a time when CEOs are rightly being encouraged to think strategically. We hear a great deal about innovation, digital transformation, artificial intelligence, expansion, new markets, disruption and long-term strategy. All of these deserve the CEO’s attention. But there is a danger in confusing strategic leadership with stepping away from the everyday responsibility of steering the business. A CEO may be thinking five years ahead while the company is struggling with a problem that requires attention today.

Strategy is important. Supervision is also important. Vision is important. Execution is equally important.

A CEO’s responsibility is not simply to decide where the corporate ship should be going. The CEO must also know whether the ship is still seaworthy, whether the crew is doing what it should, whether resources are being wasted and whether the business is actually moving in the intended direction.

September therefore provides an excellent opportunity for CEOs to bring their teams together, not for another ceremonial meeting where everyone presents slides and says everything is “on track”, but for five honest conversations that can determine how the business closes for the year.

1. “Are We Really Going to Hit Our Numbers?”

This may be the most uncomfortable conversation of all but it is also one of the most important.

The CEO needs to ask:

“Given where we are today, are we realistically going to achieve the targets we set at the beginning of the year?” The core word is ‘realistically.’ It is easy for a management team to remain optimistic. Salespeople are trained to believe that the next customer is just around the corner. Managers may be reluctant to admit that a target is no longer achievable. Nobody wants to be the person who tells the CEO that the ambitious plan agreed in January  and further emphasised in June is in trouble.

But leadership requires more than optimism.

Imagine a company that set a ₦500 million revenue target for the year. By the end of August, it has generated ₦260 million. The sales manager says: “The last quarter is usually our strongest. We should be able to catch up.”

The CEO should not dismiss the possibility but he needs to ask some follow-up questions. “What exactly will generate the remaining ₦240 million?” Which customers are expected to buy? Which contracts are already at an advanced stage? How much has been invoiced? How much has actually been collected? Which expected sales have been delayed? What happened to the opportunities that were supposed to close in the first and second quarters? What has changed in the market?

This is where a CEO separates hope from evidence.

Perhaps the business has been affected by rising transportation costs, or maybe the imported inputs have become more expensive. Perhaps customers are taking longer to pay or the sales team has been giving discounts simply to keep volume moving. These are genuine business realities that should lead to a revised strategy, not a vague promise that “things will improve.”

The conversation should end with a recovery plan. Perhaps certain products need greater attention or the company might want to concentrate on existing customers rather than spending scarce resources chasing cold prospects. Sometimes, management may need to revisit pricing or break down sales targets into weekly or monthly milestones.

Discovering the problem in September is better than discovering it in December.

2. “Where Are We Losing Money Without Realising It?”

Many CEOs know their revenue figures but only a few can confidently identify all the places where money is leaking from the business. A company can increase its sales and still become financially weaker. Consider a distributor whose turnover has grown significantly. On paper, this looks like excellent performance. But a closer examination reveals that customers are taking longer to pay, transportation costs have increased, damaged goods are not being properly accounted for, salespeople are giving discounts without sufficient controls, and inventory is sitting too long in the warehouse.

The business is busy but is it profitable? This is the kind of question a CEO needs to ask before the end of year. “Where are we losing money?” The answers may not always be dramatic. It may be the generator that runs longer than necessary because electricity supply is unpredictable. It may be fuel consumption that nobody is monitoring closely. It may be excessive use of consultants or old subscriptions that nobody remembered to cancel. It may be poor inventory management or products being damaged because of inadequate storage. It may be big customers who have owed money for six months but continue receiving goods because they take large numbers. It may be redundant staff looking busy but actually producing little results.

In some businesses, particularly growing family-owned enterprises, there is another leakage that is rarely discussed openly: the mixing of business money with personal money. The business pays school fees, household expenses, personal travels and other family obligations without proper separation from company finances. By the end of the year, the owner knows that money has gone out but cannot clearly determine what the business actually cost to run.

The answer is not to cut everything.

A CEO should ask a more intelligent question: “Which costs create value, and which costs simply consume cash?” Cutting the wrong cost can damage a business. Removing customer service staff may reduce payroll but increase customer complaints. Buying cheaper raw materials may reduce procurement costs while increasing defects. Reducing maintenance may save money today while creating a much larger repair bill tomorrow. The objective is therefore not cost-cutting for its own sake.

It is cost discipline.

September is a good time to identify the leakages because there is still enough time to plug them before the business closes for the year.

3. “What Are Our People Not Saying?”

This may be the conversation that separates a CEO that is merely competent from a truly perceptive one.

CEOs often ask their teams:

“Is everything okay?” “Are we good?” And employees always affirm that they are okay.

That answer may be completely untrue.

Sometimes employees say everything is fine because they do not believe anything will change. Sometimes they are afraid of being labelled difficult. Sometimes the CEO is surrounded by senior managers who unintentionally filter uncomfortable information before it reaches the top. And sometimes the CEO has created a culture in which disagreement is interpreted as disloyalty.

A better question is: “What is making it difficult for you to do your best work?”

That question can open an entirely different conversation.

Perhaps the sales team is being given targets without the resources required to achieve them. Perhaps employees are spending hours getting approvals for simple decisions. Perhaps a good member of staff is carrying the responsibilities of three people because two positions have remained vacant. Perhaps customers are becoming increasingly difficult because the company’s own processes are frustrating them. Perhaps younger employees feel that their ideas are ignored. Perhaps older employees feel that new technology is being introduced without adequate training. Perhaps managers are exhausted but reluctant to say so because everyone is expected to appear strong.

A CEO should also ask: “What problem have we been tolerating for too long?” The answers can be revealing. This is particularly important in businesses where hierarchy is strong. Employees may not tell the boss that a policy is failing simply because the boss appears convinced that it is working. A CEO does not have to accept every complaint as truth. But every recurring complaint deserves investigation.

And there is another useful question: “Who on this team has the capacity to do more, and who needs support?” Some employees need training while some need recognition. Occasionally, some need to leave. Good leadership is not about keeping everybody comfortable. It is about creating the conditions in which the right people can perform well.

4. “Which Customers, Products and Opportunities Deserve Our Attention Before December?”

A business cannot pursue everything.

Yet many entrepreneurs try. Every potential customer becomes important. Every new product appears attractive. Every business opportunity seems worth exploring.

By September, however, the CEO should be asking the team to make choices. Where should we concentrate our resources for the rest of the year? Which customers are most valuable? Which existing customers have the potential to buy more? Which proposals are closest to conversion? Which products have the best margins? Which services consume enormous amounts of staff time but produce little profit? Which dormant customers could realistically be reactivated? Which opportunities should we stop chasing?

That last question is particularly important. Sometimes CEOs believe that abandoning an opportunity means admitting failure. It does not. It may simply mean recognising that the opportunity no longer makes commercial sense.

Imagine a company spending months pursuing a large customer who continually demands deeper discounts, extended credit and special delivery arrangements. Winning the contract would increase turnover, but it could also consume working capital and management attention.

The CEO needs to ask: “Do we want this customer because they are valuable, or because their name looks impressive on our customer list?”

The same thinking should apply to products. A product may be popular and still be unprofitable. A service may generate plenty of activity and still produce inadequate returns. A branch may be busy and still be financially weak. Volume is not the same thing as value.

The final months of the year are not the time to spread the organisation thinly across too many priorities. Sometimes finishing strongly means doing less but doing the right things much better.

5. “What Must We Fix Before January?”

The fifth conversation takes the business beyond December. The CEO should ask: “What problem must we not carry into the new year?”

Every business has something that needs to go with the old year.

It may be poor cash collection, unreliable financial reporting, a weak sales pipeline or excessive dependence on one customer. For some, it may be an underperforming branch, technology system that no longer supports the business or absence of proper internal controls.

Whatever the problem is, January will not magically solve it. This is why the CEO should identify the issues that must be resolved before the new year begins. Not every problem can be solved in four months but it can be acknowledged, prioritised and assigned an action plan. That alone can make the difference between entering a new year with momentum and entering it carrying the unresolved baggage of the previous one.

In a nutshell, the CEO should not wait for December to tell him what September already knows. He should start early to identify and solve the problems so that the business will not fall into the cliché end of year panic where CEOs wait till end of November to start putting pressure on their staff. Suddenly everyone is asking why sales are below expectations. Finance unit starts chasing unpaid invoices with vigour. Managers are producing emergency reports and demanding extra hours from the staff. Everyone is looking for someone to blame. And the organisation starts making hurried decisions simply because there is no longer enough time to make thoughtful ones.

The CEO who is thinking about expansion into another market must know whether the current operation is profitable. If he is considering artificial intelligence, he must know whether employees are struggling with basic processes. The CEO planning a new branch must first ascertain that the existing branches are properly controlled. He must have sufficient contact with the business to know what is happening. That is what makes strategy useful.

September is therefore not simply another month on the calendar. It is a checkpoint because whatever the CEO discovers, there are still months to correct the course and fix the process.

So, before the year disappears into December, bring the team together. Ask the uncomfortable questions. The end of the year should not be a surprise. It should be the result of decisions made deliberately, beginning now.

Fatherhood with Ibe

I Once Met A Man… Who Was Always ‘Almost Home’

I have shared a few stories about accidental meetings with men and the lessons that I learnt from them. In this episode, I write about a man who sold insurance out of a briefcase that never seemed to close all the way. I met him way back, in my very early 20s, studying for my Masters degree at Harvard. I used to pick up little jobs that could fit into my schedule and provide the extra cash for things not covered by the scholarship that supported my studies. That period, I was working the counter at a diner off Route 9, the kind of place where the coffee was always a little burnt and nobody minded. His name was Walter, and he came in most weeknights around eight, ordered the same thing; meatloaf, black coffee, no dessert, and sat in the corner booth doing paperwork until the diner shut its doors.

I was young enough then to think a man alone in a diner every night was either sad or mysterious; I hadn’t yet learned that most of the time it’s a combination of both.

One night, business was slow and I took his second cup of coffee to him. I could no longer hold back my curiosity so I asked him a question tactlessly, the way only the young and unafraid of consequences can be.

“Do you have a family, Sir?” I’d asked. He looked up at me over his reading glasses, and I remember thinking he seemed surprised anyone had noticed him enough to ask. His face seemed to go through a number of emotions, all of which told several stories.

Calmly, he nodded and told me he had a family. I then asked the real question on my mind, why wasn’t he ever home with his family?

“Long story!” He said after a long pause, waving to the seat opposite his. I sat down.

“You don’t have children?” I’d asked, intrigued. He didn’t look at me, he picked his coffee mug took it to his mouth, seemed to think better of it, and then carefully put it back on the saucer.

“I’ve got a boy,” he said. “He is eleven years old. Best kid ever.” Then he went quiet for another ten seconds, like he was deciding whether I’d earned the rest of the sentence. “I tell myself every night I’ll be home by seven. Every single night! And every single night something comes up. Sometimes it’s a client with a policy that needs revising, other times, it’s a call I have to return before it’s too late to call anyone back.”

“Every day?” I’d asked. “Nobody works like that every single day.”

He looked at me and shook his head. He told me that it was a very competitive world out there and to make it, a man had to be immersed in the job.

I asked him what he was working so hard for. That seemed to surprise him. He looked at me with a frown and quickly looked back into his coffee as if the answer was in the dark brew.

“For him,” Walter said, letting out a deep breath, like the answer had been sitting right there in his mouth the whole time but he’d just never said it out loud. “So he has what I didn’t have.”

I didn’t say anything else that night. I was 21 and didn’t know enough to know what else to say. But Walter kept coming in, week after week, and slowly, the way ice melts without you noticing until suddenly there’s a puddle, he started talking more. He told me about his son Danny; how Danny had started drawing these elaborate comic books, whole worlds full of characters, and how he had promised Danny that he would read the newest one every Friday. He told me about missing three Fridays in a row. He told me how Danny had stopped asking him to read them.

“He didn’t get angry,” Walter said, and this was the part that stuck with me, the part I still turn over decades later.

“Anger would’ve almost been easier.” Walter said, his voice thick with emotions. “He just stopped asking. It was like he’d filed me under ‘busy’ or ‘unavailable’ and moved on. Eleven years old, and he’d already learned not to expect me.”

I remember asking him, again with that reckless honesty of youth, why he didn’t just stop procrastinating. I asked him what it would cost him to sell fewer policies but make it home at 7.00pm like he wanted.

“I’m scared,” he admitted, and it was the first time I’d heard a grown man say those words about anything that wasn’t a monster or a war. “I’m scared that if I’m not building something for him, I’m not worth anything to him. I don’t know how to just be there. Providing, I understand. Being there, doing nothing, just sitting on the floor while he draws his little worlds,” he threw up his hands in a gesture of total confusion. “I don’t know what I’m supposed to do with my hands while he does that.”

That was the winter I stopped seeing Walter come in. I assumed he’d found a different diner, or maybe his route or routine had changed. Then, nearly a year later, he walked in on a Tuesday night, I was working on my doctoral thesis then and gave the diner fewer hours. I almost didn’t recognise Walter. He looked like a different man. He did not look younger exactly, he looked lighter, like he’d set something down that he’d been carrying so long he’d forgotten it had heavy weight.

We greeted like old friends and I asked about his son. He told me Danny had gotten sick.

“It was nothing life threatening, thank God,” he said quickly when my alarm nearly gushed over. “He had a bad flu that turned into pneumonia and landed him in the hospital for four days.”

Walter said he had sat by that bed for all four days, briefcase left at home, phone turned off in his coat pocket, praying all the prayers he could.

“I made promises to God and to myself that I would treasure every moment with my son if he got out of that hospital bed. I told Danny to get well and I would buy whatever he wanted.”

“You know what he wanted?” Walter asked me. I shook my head. “He didn’t want me to bring him anything. He didn’t want me to promise anything. He just wanted me to sit there, with him. That’s it. Just sit there and exist next to him.”

Walter told me that on the second night, half-asleep in the hospital chair, Danny had asked him, in that groggy, unguarded way sick kids talk, why he worked so much. And Walter, too tired to give the rehearsed answer, had just said, “I don’t know, buddy. I think I forgot how to stop.”

“And he said,” Walter told me, his voice catching in a way I’d never heard from him before, “‘I don’t need more stuff, Dad. I just need you to be with me a little more.’ I didn’t know when tears rolled down my cheeks.” He said emotionally, reliving the moment.

Walter said he left the insurance company not long after that. He handed off his clients to a younger agent hungry for the workload Walter used to carry like a badge. He said he later took an administrative position in another company and cut down his hours. He started reading the comic books again on Fridays. He told me Danny started drawing him into them — a character called Papertrail Man, whose superpower was showing up exactly when you needed him to.

I think about Walter more than almost anyone else I met in those diner years. Not because his story was unusual — it wasn’t, not really, I’ve since met a hundred men just like him — but because he was the first person who taught me something I didn’t understand yet at nineteen and have spent the rest of my life understanding more each year: that providing and being present are not the same gift, and a child can’t unwrap the first one if you never hand over the second.

Walter passed a few years back. Danny, a grown man himself now, with kids of his own, spoke at the funeral. He didn’t talk about the insurance policies or the house Walter had paid off or any of the provision. He talked about Fridays. He talked about a man who learned, late but not too late, how to sit in a room and simply exist next to the people he loved.

That’s the first time I ever learned about the adult’s fear of failure and the near emotional paralysis that comes from that fear. Walter loved his son dearly but fear of failing the child drove him further away, nearly breaking the bond between them. I share this story because there are many fathers like Walter; giving so much time to their jobs and businesses but very little to their families. They fear that they may lose the respect and love of their family if they lose the strength of their wallet. Some are lucky like Walter and remedy their family conflict. Some others are like Tijani who found out too late that all the money in the world cannot replace the presence of a father in the lives of his children.

Next publication, I will tell the story of Tijani and the lesson he learnt the harshest way.