Chapter 7: Honest Advisers and Pleasant Flatterers

The Idea Everyone Loved

Solveig is fifty and owns two small flower shops. She built the business over twenty years, starting with a single stall at a weekend market. She has twelve staff, and they are loyal and hard-working. Solveig is proud of the friendly atmosphere in her shops. Her staff like her, and she likes them.

Last year, Solveig had an idea. She would start a subscription service: customers would pay a monthly fee and receive fresh flowers at their door every week. She was excited about it, and she presented it to her staff at a meeting. Everyone said it was a wonderful idea. Nobody raised any concerns. Solveig invested a large amount of money in a delivery van, special packaging and advertising.

The service failed. Within six months, it was losing money every week. The flowers often arrived damaged, because the packaging did not protect them well enough on the road. Many customers cancelled after a month or two, saying that they had too many flowers. The delivery routes took far longer than planned. Solveig had to close the service and sell the van at a loss.

Afterwards, while clearing out the delivery packaging, Solveig talked with one of her longest-serving staff members, a quiet man named Kristoffer, who had been with her for fifteen years. She asked him what he thought had gone wrong. He hesitated, then said, "I worried about the packaging from the beginning. Flowers do not travel well in boxes. And I thought weekly might be too often for most people." Solveig stared at him. "Why did you not say so at the meeting?" Kristoffer looked at the floor. "Everyone was so enthusiastic," he said. "And you were so excited. I did not want to spoil it."

Solveig realized that her friendly, loyal staff had not been giving her advice. They had been giving her approval. She had surrounded herself with people who told her what she wanted to hear, not because they were dishonest, but because the atmosphere she had created made disagreement feel unkind. Machiavelli wrote about exactly this danger in his chapters on advisers and flatterers.

Judged by the People Around You

In chapter 22 of The Prince, Machiavelli turns to the people a ruler chooses to help him: his ministers and advisers. He says that choosing them is no small matter, because they will be good or bad according to the ruler's own wisdom. Indeed, the first impression people form of a ruler's intelligence, he says, comes from looking at the people around him. If they are capable and loyal, the ruler can be considered wise, because he knew how to recognize their ability and keep their loyalty. If they are not, people will judge him poorly, because his first mistake was in choosing them (The Prince, chapter 22).

Machiavelli adds an observation about three kinds of minds. One kind understands things by itself. A second kind can recognize good thinking when others present it. A third kind can do neither. The first, he says, is excellent; the second is also excellent; the third is useless (The Prince, chapter 22). His point is that a ruler does not need to have every good idea himself. It is enough, and very valuable, to be able to recognize good advice when he hears it, and to choose people who can give it.

This observation is comforting for ordinary people. Most of us are not geniuses who see everything clearly on our own. But we can learn to be the second kind of mind: someone who listens to others, weighs what they say and recognizes when they are right. In working life, this is often more valuable than brilliance, because no one person can see every side of a problem.

The same idea applies to us even if we are not leaders. Each of us has, in a sense, a circle of advisers: colleagues, friends, mentors and family members whose opinions we seek and whose words influence our decisions. The quality of that circle matters a great deal. A person surrounded by honest, thoughtful advisers will usually make better decisions than a person surrounded by people who simply agree.

Solveig's first mistake, in Machiavelli's terms, was not in choosing bad people. Her staff were good people. Her mistake was in creating an atmosphere in which good people did not feel able to give honest advice. This leads to Machiavelli's next chapter, on flatterers.

The Plague of Flatterers

In chapter 23 of The Prince, Machiavelli warns against a danger that he says almost every ruler faces: flatterers, of whom, he says, courts are full. People take such pleasure in their own affairs, and deceive themselves so easily about them, that it is very hard to defend against this plague (The Prince, chapter 23).

Machiavelli then explains the difficulty. The only way to guard against flatterers is to let people understand that telling you the truth will not offend you. But if everyone can tell you the truth at any time, he worries, respect for you may decline. So he recommends a middle way. A wise ruler should choose a few wise people and give them, and only them, the freedom to speak the truth to him, on the matters he asks about. He should ask them about everything, listen to their opinions and then make his own decision, alone. With these advisers, he should behave in such a way that each of them knows that the more freely they speak, the more welcome they will be (The Prince, chapter 23).

Machiavelli adds that a ruler should be a great asker, and a patient listener to the truth about the things he has asked. Indeed, if he notices that someone is holding back the truth out of fear or respect, he should be displeased. And he concludes with an important point: good advice, from whoever it comes, has its origin in the wisdom of the ruler, not the wisdom of the ruler in good advice. In other words, a person who does not know how to seek and use advice will not be saved by good advisers, because they will not recognize good advice when it comes (The Prince, chapter 23).

Some of this advice belongs to a world of princes and courts, and we can adapt it. In modern working life, it is usually better if everyone in a team feels able to raise concerns, not only a chosen few. Common sense and everyday experience suggest that teams in which people feel safe to speak up about problems and mistakes are more likely to catch errors early. But the heart of Machiavelli's advice remains sound: ask often, listen patiently, make it clear that honesty is welcome and then take responsibility for your own decision.

Notice, too, that Machiavelli puts the responsibility on the person seeking advice, not on the advisers. Solveig's staff did not fail her. She failed to make it safe for them to disagree. In Machiavelli's terms, she was not yet a great asker and a patient listener. This is a hopeful point, because it means that each of us can improve the advice we receive by changing how we ask for it.

Solveig Learns to Ask

After the subscription service failed, Solveig thought carefully about how she had presented it. She had announced it with great excitement, as something already decided. She had asked, "What do you think?", but in a way that made it clear she hoped for enthusiasm. Nobody had felt free to say, "I have doubts."

When Solveig had her next idea, a small range of potted plants for offices, she approached it differently. She did not present it as a plan. She presented it as a question. At a staff meeting, she said, "I am thinking about selling plants to offices. Before I decide anything, I need to know what could go wrong. Please tell me every problem you can think of. I will be grateful for every doubt."

At first, there was silence. Then Kristoffer raised his hand and mentioned that offices often have poor light, which kills many plants. Another staff member said that offices would want someone to water the plants, which would require regular visits. A young part-time worker pointed out that several garden centres already supplied offices and might be cheaper. Solveig thanked each person warmly and wrote down every point.

With this information, Solveig redesigned the idea. She chose only plants that survive in low light, offered a monthly care service for a small additional fee and focused on small offices near her shops, which garden centres did not serve well. She started with five customers as a test before investing more. The service grew slowly and steadily, and after a year it was profitable.

Solveig also changed something more lasting. She began to thank people publicly for raising concerns, not only for good ideas. She asked Kristoffer, who had the most experience and the sharpest eye for problems, to be her "doubt-raiser" for new plans: someone whose role was to look for weaknesses. "I used to think a happy team was one where everyone agreed with me," she says. "Now I think a happy team is one where everyone feels safe to disagree. The shops are still friendly. They are just honest too."

Hamza Learns to Be an Honest Adviser

Hamza is twenty-seven and works as an assistant to the director of a small museum. His director, a passionate and energetic woman named Eleonora, often asks his opinion about her plans: exhibitions, events, ways of attracting visitors. Hamza admires her greatly, and for his first year he always agreed with her ideas. It seemed respectful, and it kept the relationship smooth.

But Hamza began to feel uneasy. Some of Eleonora's plans seemed unrealistic to him: exhibitions that would cost more than the budget allowed, events scheduled at times when few people could come. He saw problems, but he said nothing. When some of these plans ran into difficulties, he felt guilty, as if he had let her down.

Hamza realized that Machiavelli's chapter on flatterers applied not only to leaders but to the people who advise them. He had been a flatterer, not because he wanted anything, but because he was afraid of disappointing someone he admired. And this was not loyalty. Real loyalty, he decided, meant telling her the truth, respectfully.

Hamza began to practise honest advice carefully. When Eleonora asked his opinion, he first mentioned what he liked about the idea, honestly. Then he raised his concerns clearly but gently: "I think the theme is wonderful. I am worried that the cost of the lighting might be more than we have. Could we look at the numbers together?" He always offered to help find a solution, so that his concerns did not feel like a wall.

Eleonora's response surprised him. She thanked him and said that she had been hoping someone would tell her when her enthusiasm ran ahead of reality. "Everyone here agrees with me," she said. "It is very lonely. I need someone who will tell me the truth." Hamza's role changed. He became her trusted adviser, and she began to ask his opinion on more important matters. He discovered that honest advice, offered respectfully and with a willingness to help, was far more valuable to her than agreement.

Hamza also learned to choose his moments. He did not raise every small doubt, because constant objections would have worn Eleonora down and made his concerns easier to ignore. He saved his honesty for the matters that really counted: large costs, risks to visitors, plans that could damage the museum's reputation. On smaller matters, where the risk was low, he let her enthusiasm lead. An honest adviser, he realized, is not someone who disagrees with everything, but someone whose disagreement means something when it comes.

Priscila Seeks Feedback on Her Practice

Priscila is thirty-five and works as a midwife in a hospital maternity unit. She is experienced and confident, and the women she cares for often praise her warmth. But she has noticed that she rarely receives honest feedback about her clinical work. Patients are grateful and kind. Colleagues are busy. Her annual reviews are positive but general. She wonders whether there are things she could do better that nobody mentions.

Priscila realized that, like Solveig, she was surrounded by people who were kind to her but who did not tell her the truth about her work, not because they were dishonest, but because there was no habit of honest feedback. She decided to choose a few wise advisers, in Machiavelli's sense, and to ask them directly.

She approached an older midwife whom she deeply respected and asked whether she would be willing to observe her work occasionally and give her honest feedback. She also asked a doctor she trusted to tell her if he ever noticed anything she could improve. And she began to ask the women she cared for, at the end of their stay, one specific question: "Is there anything I could have done better for you?"

At first, the answers were mostly kind and general. But because Priscila asked repeatedly and listened without becoming defensive, people began to share more. The older midwife pointed out a small habit in how Priscila explained procedures that sometimes confused frightened women. The doctor suggested a way of recording information that would help the night staff. One mother told her that she had felt rushed during a difficult moment, which Priscila had not noticed. Each piece of feedback was uncomfortable, but each helped her improve.

Priscila says that the hardest part was learning to listen without defending herself. "My first instinct was always to explain why I had done something," she says. "But Machiavelli's idea of being a patient listener helped me. I learned to say only, 'Thank you, I will think about that,' and then to think about it later. People started telling me more once they saw that I would not argue." She now feels more confident in her work, not less, because she knows that her advisers will tell her if something is wrong.

Viggo and the Room of Nodding Heads

Viggo is forty-four and manages a department of twenty people in an organization that runs public swimming pools and sports centres. He is intelligent, decisive and confident, and he expresses his opinions strongly. In meetings, he often states his view at the beginning and then asks whether anyone disagrees. Almost nobody ever does.

Viggo had always taken this as a sign that his decisions were good. But a new member of his team, who had worked in other organizations, told him privately after a few weeks that people in the department often disagreed with his decisions but felt they could not say so, because he spoke so strongly at the start of every meeting. "By the time you ask for opinions," she said, "everyone already knows what you want to hear."

Viggo was surprised and a little offended. But he decided to test what she had said. At the next meeting, he described a problem without giving his own view and asked each person in turn to give their opinion before he spoke. The discussion that followed was the most varied and useful he had heard in years. Several people suggested solutions he had not considered. One of them was better than the solution he had planned to propose.

Viggo changed his meeting habits. He now speaks last on important decisions, after hearing from others. For major plans, he sometimes asks one person to argue deliberately against the plan, so that its weaknesses are examined. He still makes the final decision, as Machiavelli advised, and he still expresses his view clearly. But he no longer speaks first. "I thought I was asking for advice," he says. "Actually, I was asking for agreement. The two sound similar, but they produce very different answers."

Viggo's story shows that flattery is not always deliberate. Often, it is produced by the way questions are asked. A leader who states a strong opinion first, who reacts badly to disagreement or who only asks when the decision is already made will receive agreement, whatever people really think. Changing the way we ask can change the truth we hear.

Practical Steps: Becoming a Great Asker

The first step is to ask before you have decided. When you seek advice, do so while the decision is still open, and say so. "I have not decided yet. I need your honest view." Advice sought after a decision is made usually turns into approval.

The second step is to ask specifically for problems. Instead of "What do you think?", ask "What could go wrong?" or "What am I missing?" or "What would you do differently?" These questions give people permission to raise concerns, which many will not do otherwise.

The third step is to speak last. If you lead a group, share your own view only after others have spoken. If you are asking one person, try not to reveal what you hope to hear. This reduces the pull toward agreement.

The fourth step is to listen patiently and thank people for honesty. When someone raises a concern, do not argue or explain at once. Say, "Thank you, that is helpful," and think about it later. Thank people for doubts, not only for agreement. Machiavelli advised rulers to make it clear that the more freely advisers spoke, the more welcome they would be.

The fifth step is to choose a few trusted advisers. Identify two or three people whose judgment you respect and who will tell you the truth: a colleague, a mentor, a friend outside your workplace. Ask them regularly. Like Priscila, you may need to ask several times before people believe you really want honest answers.

The sixth step is to decide for yourself. After hearing advice, take responsibility for your decision, as Machiavelli advised. Advisers inform; they do not decide. A person who simply follows the last advice they heard is not using advice well. A person who weighs advice carefully and then decides is.

Honest Is Not Harsh, and Advice Is Not Surrender

Two limits are worth stating. First, honest advice does not need to be harsh. Hamza learned to begin with what he genuinely liked and then to raise concerns gently, with an offer to help. Kristoffer could have said, "I wonder whether the packaging will protect the flowers on the road," which is honest and kind. People who confuse honesty with bluntness often find that their advice is rejected, not because it is wrong, but because it is delivered in a way that makes others defensive.

Second, seeking advice does not mean giving up responsibility. Machiavelli was clear that a wise ruler listens to advice and then decides alone. Some people, afraid of making mistakes, ask so many people for advice that they never decide, or they choose whatever the last person said, so that they can blame someone else if things go wrong. This is not wisdom. It is a way of avoiding the courage that decisions require.

It is also worth remembering that not all advice is good advice. Some people give advice that serves their own interests. Some give confident advice about matters they do not understand. Machiavelli warned that an adviser who thinks more of himself than of you is not a good adviser (The Prince, chapter 22). Part of being a great asker is learning whose advice to trust, by watching over time whose advice has proved sound.

A Short Exercise: Your Circle of Advisers

This exercise helps you see who advises you, and how honestly. It takes about fifteen minutes.

Take a page and write down the names of five to eight people whose opinions you often seek about your work. They might be colleagues, managers, friends, family members or mentors. Next to each name, write two things. First, does this person usually tell you what you want to hear, or what they really think? Second, has their advice usually proved sound?

Look at your list. Do you have at least two or three people who tell you the truth and whose advice has proved sound? If not, think about who in your life might become such an adviser, and write their names at the bottom.

Next, think about how you ask for advice. Write down one habit that might be producing agreement rather than honesty: speaking first, asking after deciding, reacting defensively to criticism, asking only people who agree with you. Then write one change you will try in the coming month.

Finally, choose one decision you are facing now, and ask one honest adviser for their view, using a specific question such as "What could go wrong?" Write down what they say, without arguing. After you have decided, look back and note whether their advice changed your decision. Solveig did this exercise after the failed subscription service. Her list showed that almost all her advisers were people who agreed with her. She added Kristoffer and her accountant to her list of honest advisers, and she now asks both of them, "What could go wrong?", before every major decision.

Chapter Summary

In chapter 22 of The Prince, Machiavelli wrote that people judge a ruler's intelligence by the people around him, and that being able to recognize good advice from others is an excellent kind of mind. In chapter 23, he warned against flatterers, advising rulers to choose wise advisers, give them freedom to speak the truth, ask often, listen patiently and then decide for themselves. Good advice, he said, comes from the wisdom of the one who seeks it. In modern workplaces, it is usually best if everyone feels safe to raise concerns.

Solveig and the idea everyone loved, Hamza learning to advise his director honestly, Priscila seeking feedback on her practice and Viggo in his room of nodding heads all found that the advice we receive depends greatly on how we ask for it. Asking before deciding, asking specifically for problems, speaking last, thanking people for honesty and then deciding for ourselves can turn approval into real advice. Honest advice need not be harsh, and seeking advice is not giving up responsibility.

In the next chapter, we will look at what Machiavelli called the most difficult thing of all: introducing new ways of doing things.