PDF Summary:Necessary Endings, by Henry Cloud

If you’ve ever struggled to leave a lousy job or a toxic relationship, psychologist Henry Cloud has advice for you. In Necessary Endings, Cloud argues that pulling out of a bad situation is often the best way to move forward with your life. According to Cloud, we should view the endings in our lives positively, as those endings enable us to begin to live the lives we want. Cloud offers strategies for assessing the various situations in your life, determining which of them need to end, and making sure that your endings stick.

In our guide, we’ve distilled Cloud’s actionable advice for making changes in your life. We’ve also included commentary from the worlds of business and psychology that adds more nuance and detail to Cloud’s ideas about business, life, and boundaries.

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To assess whether your employees are being set up to fail, consider the quality of their relationships with management. If these relationships became strained at the same time as performance dropped, it may be a sign that your employees have been set up to fail.

Use Character to Assess Relationships

Once you’ve considered the structural factors at play, assess relationships based on your impression of the other person’s character. Cloud claims that character is predictive of whether or not people will be receptive to change and feedback.

(Shortform note: According to some psychologists, people tend to overestimate the relationship between another person’s actions and their character. These psychologists suspect that we overestimate our knowledge of others due to an inherent tendency to view ourselves as being more complex than others. These kinds of cognitive biases may complicate the process of judging someone’s character.)

According to Cloud, people can generally be sorted into three categories based on their character. There are responsible people, irresponsible people, and dangerous people. Cloud offers different strategies for dealing with each type of person. (Cloud notes that people are too complicated to truly fall into three simple categories; however, these three categories can still be a useful heuristic for determining which relationships to end.)

(Shortform note: Many psychologists have created systems for comparing personality types, each with its own strengths and weaknesses. For example, the Myers-Briggs Type Indicator (MBTI), which is widely used in the business world, sorts people into 16 types. Supporters of the MBTI argue that it helps companies support employees, but critics note that there’s little scientific evidence that supports the MBTI. Other researchers believe that there are four personality types, though they note that there are numerous other ways to group people.)

1) Responsible people (Cloud refers to them as “wise people”): Responsible people are characterized by their ability to take ownership of their actions. They’re able to admit and apologize when their mistakes have hurt others, and they readily incorporate feedback and change unwanted behaviors.

Responsible people are by far the easiest group to deal with. Relationships with responsible people are often improved by open communication—if you tell them what they’re doing wrong, they’re likely to correct it on their own. Responsible people reward your investments in relationships with them. They benefit from coaching and education more than others. If you’re dealing with a responsible person, communicate openly and honestly, and you’re unlikely to have to end the relationship.

Help Your Employees Behave Responsibly

According to business psychologists, employees with a sense of ownership in the company behave more responsibly and productively. To increase the sense of ownership among your employees, these experts recommend assigning employees projects that affect their roles and allowing them to work on a given project from start to finish. These measures help your employees invest in their day-to-day tasks, encouraging them to act responsibly.

As you enact measures to help your employees feel a sense of ownership, you should also strengthen your relationships with your employees. Business coaching experts note that employees only respond positively to coaching when managers understand their desires and motivations. As you get to know your employees more personally, request feedback on how best to support them—this information will help you to coach them more effectively in the future.

2) Irresponsible people (Cloud refers to them as “fools”): As you might expect, irresponsible people are in many ways the polar opposites of responsible people. Irresponsible people are unable to take responsibility for their actions, instead finding an external factor to blame for any mistakes they make. When pressed about their behaviors, they’ll deflect or become heated and defensive.

(Shortform note: Psychologists note that defensive behavior often coincides with a neurological fight-or-flight response. In other words, people react defensively as a way of protecting themselves when feeling threatened. In these moments, people who get defensive feel that your criticism of their behavior is an attack on them as a person—in response, they use defensive tactics to try to protect themselves.)

When dealing with irresponsible people, it doesn’t always help to communicate directly about problem behaviors. Instead of critiquing specific misbehaviors, Cloud recommends calling out their overall inability to accept responsibility for their action. Point out to irresponsible people that they always find someone or something else to blame when things go wrong—this can sometimes help them change their patterns. Setting consequences also works well with irresponsible people, as it forces them to bear the weight of their own mistakes, which encourages them to change their behavior.

For example, suppose you’re struggling with an employee who habitually misses deadlines. Not only is this employee always behind schedule, they always have an excuse, always finding something or someone else to blame for their lateness. According to Cloud, trying to talk to them about their time management will be ineffective, as they’ll only continue to deflect responsibility. Instead, point out to the employee that they’re never accountable for their mistakes, and that their pattern of making excuses makes it difficult to manage them. By making them aware of their cycles of irresponsibility, you may help them begin the process of breaking those cycles.

It may not always be possible to improve relationships with irresponsible people. If you’ve tried communicating and setting consequences to no avail, Cloud recommends putting up boundaries to protect yourself. In some cases, this might mean bringing the relationship to an end.

Set Boundaries With Irresponsible People

Just as Cloud opines that consequences help irresponsible people change their behavior, in Set Boundaries, Find Peace, Nedra Glover Tawwab argues that you must enforce consequences for others to respect your boundaries.

According to Tawwab, consequences serve a dual function—they communicate to others that your needs are serious, and they protect you from people who don’t respect your boundaries. Tawwab recommends limiting your time with irresponsible people, as it both protects you by limiting your exposure to them and strongly communicates that a change is needed.

As you set boundaries with the irresponsible people in your life, be sure to speak up immediately when unwanted behaviors occur. Tawwab argues that communicating your discomfort in the moment helps to end uncomfortable situations as fast as possible, while also preventing resentment from building.

3) Dangerous people (Cloud refers to them as “evil people”): Dangerous people are completely unlike the first two groups. Whereas both responsible and irresponsible people may sometimes cause harm by accident, dangerous people intend to harm others with their words and their actions. They are unsafe to be around.

None of the strategies we have listed are effective in dealing with dangerous people. According to Cloud, nothing you can do will change their behavior. Instead, end any and all relationships with dangerous people, and do your best to keep away from them. Cloud notes that deterrents, such as legal actions or calls to law enforcement, can be effective in keeping dangerous people away.

(Shortform note: In Why Does He Do That?, Lundy Bancroft describes dangerous people as “abusers.” According to Bancroft, abusers are people who intentionally harm others to get what they want. Like Cloud, Bancroft believes serious deterrents, such as arrests and litigation, can be used to curb abusive behavior. Beyond the individual level, Bancroft argues that to deal with dangerous, abusive people, you have to fight the cultural conditions that enable their actions. According to Bancroft, abusive behavior is often fueled by social imbalances in power due to money, race, gender, disability, or other criteria. Rectifying these power imbalances makes it more difficult for abusers to target vulnerable individuals.)

Let the Other Person Decide

If, after assessing someone’s character, you’re still not certain whether to end your relationship with them, it can help to let the other person decide (Cloud refers to this process as “self-selection”). Letting the other person decide entails communicating your standards to the other person and allowing them to choose whether they want to live up to those standards.

(Shortform note: Communicate your expectations clearly when you allow the other person to decide. Leadership experts note that people can’t live up to your standards if you don’t clearly communicate them in the first place. In workplace settings, it can be helpful to create a list of “always” and “never” behaviors for employees—for example, communication procedures that must always be followed or interpersonal behaviors that are never acceptable. Creating such clear-cut criteria makes it easier for employees to decide if they want to work with you.)

Cloud points out that allowing the other person to make the decision has benefits for both parties. If you struggle with guilt when imposing consequences in relationships, allowing the other person to make the decision can help alleviate this feeling. This style of decision-making can feel more inclusive to the other person—instead of passing down behavioral mandates, you’re including them in the decision-making process.

For example, suppose you have an employee who does excellent work but is lax about deadlines. You could simply tell them to work harder, or you could let them decide. Let them know that you admire their work and want them to succeed, but in order to stay with the company, they’ll need to meet their next set of deadlines. This clarifies your expectations for the employee and puts the power in their hands. At the same time, it gives you a clear-cut, guilt-free way to decide whether to end the relationship.

(Shortform note: Experts argue that when employees are involved in decision-making processes, they tend to feel more engaged and perform better. Based on these findings, including employees in a mutual decision-making process about their role may help encourage them to rise to your standards.)

Enact Endings

Once you’ve determined that a change or an ending is needed in a particular situation, create structures that encourage you to act. Then, when it’s time to break things off, prepare carefully for that conversation. Finally, after an ending, take time to grieve, as grieving helps you process the experience and learn from it.

Create Structures That Encourage Action

As you move toward ending a situation or relationship, you’ll want to create structures that keep you engaged in the process. Cloud notes that it’s easy to lose focus when dealing with difficult situations. Because these situations are painful, we naturally want to focus elsewhere, which can lead us to delay making important changes.

To stay focused on the problem situation, regularly schedule time to work on the problem, and set deadlines for taking action. Regularly scheduling time to work on the problem helps you avoid losing focus, and setting deadlines helps ensure that you don’t delay your endings indefinitely.

It can be helpful to bring other people in to hold you accountable to your decisions. Cloud argues that people who aren’t directly involved are less likely to avoid the problem and can help to keep you motivated.

For example, if you need help ending a dead-end job, you could set a deadline with someone who will keep you accountable, such as a friend, coworker, or family member. While on your own it might be easy to delay putting in your two weeks’ notice, having a friend to call you out can help redirect your focus.

Expert Tips for Ending Problem Situations

If you’re nervous about approaching a tough situation, it may help to take a direct approach to communication. Psychologists argue that people avoid difficult conversations because they’re a lot of work for the brain to handle. To get over that mental hurdle, experts recommend a direct approach, being candid with everyone involved about your feelings regarding the situation. Immediately and directly addressing the issue opens communication and helps others to engage respectfully, even if they disagree with you.

In addition to communicating directly, create a schedule that will allow you to handle the situation with maximum productivity. Schedule time early in the day, and allot more time than you think you’ll need. Experts note that you’re more likely to be energized and productive earlier in the day. And, allotting extra time ensures that you’ll have enough time to handle things even if you’re interrupted or experience unexpected complications.

Once you’ve laid out a schedule for dealing with the problem, you’ll want to bring on another person to keep you accountable to that schedule. However, think carefully before choosing a friend. Your accountability partner should be someone who is ready to push you and call you out when necessary, and sometimes friends are simply too kind to push you as hard as you need. If you’re considering choosing a friend, think carefully about whether that person is willing to be blunt and honest enough to hold you accountable.

Focus on What You Can Control to Avoid Losing Motivation

As you take action to end things, take care not to lose your motivation to deal with difficult situations. According to Cloud, it’s easy to lose motivation when a situation includes circumstances outside of your control. The more you ruminate on unfortunate circumstances, the more you’ll feel that there’s nothing you can do to improve your situation. This leads to feelings of apathy that can stop you from acting. To avoid falling into this trap, focus on the elements of a situation that are within your control. Cloud argues that focusing on the things you can control helps to convince your brain that you have the power to influence the situation, which in turn empowers you to act.

Suppose that your business is struggling due to rising inflation. If you choose to focus on the negative effects of inflation, you’ll wind up feeling powerless, as there’s nothing you can do to steer the global economy. However, if you instead choose to focus on the things your business can do to cut costs and increase revenue during this time, you’ll likely see that you have many options for dealing with the situation.

(Shortform note: Experts note that it’s important to focus on the things you can control because doing so reduces interference, which refers to distractions that pull you out of a focused, productive state. As you focus on the things you can control, you’ll also want to avoid comparing yourself to others, which is now easier than ever in the age of social media. Comparing yourself to others leads you to focus unduly on the result, instead of the process you need to follow to get there. To avoid this, focus on your individual goals, and don’t adjust those goals or change your trajectory no matter what your peers may be doing.)

Prepare for the Ending Conversation

When it comes time to end a relationship, thoroughly prepare for the ending conversation. Cloud contends that people often go into these conversations underprepared, which leads them to make mistakes that make the process more difficult and confusing for everyone involved.

The first step in preparing for an ending conversation is to set goals for what you’d like to accomplish during the conversation. According to Cloud, people who enter these kinds of conversations without clear goals in mind often end up waffling or letting the other person convince them to change their mind. For example, if you decide to fire an employee whose role has become obsolete, your goal might be to clearly communicate that the employee is fired, while also thanking them for their time at the company and letting them know that you’re open to being listed as a reference. With these goals in mind, it’ll be easier to stay on task in the heat of the moment.

Once you’ve set goals for the conversation, it can help to rehearse. Endings can be emotional, and you may find it difficult to remember everything you wanted to say when the time comes. While it might sound silly, writing a script and practicing it can help you feel more confident later on.

When writing your script, be sure to focus on the problem in the relationship, not the person. According to Cloud, focusing on the other person’s flaws can make them feel attacked, which may result in a heated and uncomfortable conversation. By focusing on the relationship’s issues, you’ll maintain clarity without upsetting the other person as much.

During the conversation, try to balance empathy with firmness. Cloud says people are more receptive to ending conversations when you approach them gently. However, at the same time, take care not to be too gentle, as this might give the other person the impression that you aren’t serious. Don’t be cold, but don’t leave any wiggle room either.

More Advice for Effective Endings

There are a variety of perspectives on the best practices for ending personal and business relationships. In Difficult Conversations, Douglas Stone, Bruce Patton, and Sheila Heen argue for the importance of separating impact from intent. Stone, Patton, and Heen note that people who hurt you don’t always intend to and aren’t usually bad people. Separating impact from intent can help you maintain empathy for the other person as you end things.

Along with separating impact from intent, as you set goals for the conversation, remember that you can’t control the other person’s reaction. No matter how well you prepare or how clearly you communicate, how the other person reacts is up to them. Keep this in mind, and remember that it doesn’t reflect on you if the other person becomes upset or refuses to accept the ending. To avoid being upset if the other person reacts poorly, set goals that focus on your own communication and not on the other person’s reaction.

Once you’ve set goals for your communication, it’s time to practice communicating. In addition to rehearsing with a friend, experts recommend spending time by yourself to prepare for an imminent ending. During your solo rehearsal, you can coach yourself and prepare mentally for the task ahead. Spending time preparing alone can help you to understand and accept your role in the failed relationship, as well as giving you time to further meditate on why the ending is needed.

As you rehearse for an ending conversation, write a script that succinctly addresses your issues in the relationship. Take care not to over-explain your reasoning. Getting too detailed when explaining your reasons for ending a relationship creates room to argue, and may bring up hard feelings that can lead to escalation.

Once you’ve taken all the necessary steps to prepare for the conversation, let your loved ones know what’s about to happen. By letting your loved ones know in advance, you’ll ensure that you have the support you need when you come out of the conversation.

Take Time to Process and Reflect

After ending a situation or relationship, take time to process your feelings and reflect on the situation and its ending. Cloud argues that taking time to process your emotions after an ending is an essential part of the process. Processing and reflecting on the situation can help you to learn from it. As you reflect, make an effort to understand what went wrong. Doing so will help you avoid similar situations in the future.

(Shortform note: While it’s important to reflect on relationships after they end, experts caution against hashing out the relationship with your ex. It can be tempting to meet up with your ex to discuss exactly what went wrong, but these meetings only lead to more conflict, and in some cases, they may even lead you to reopen a relationship that you worked hard to end.)

By contrast, when you avoid reflecting on your feelings, you’re liable to make the same mistakes again. Not only this, but when you avoid processing your feelings and instead choose to avoid them, you’re also more likely to make impulsive decisions to distract you from your pain.

(Shortform note: To avoid making impulsive decisions after ending a romantic relationship, some experts suggest setting aside a period of time to take a break from dating. Taking a break from dating gives you time to focus on yourself and on unpacking your feelings about the ending. Explicitly deciding to stop dating helps ensure that you don’t allow yourself to be distracted by a sudden rebound fling.)